Synthetic applications of Passerini reaction

Current Organic Chemistry

Volumn 16, Issue 4, 2012, Pages 418-450

  Kazemizadeh, Ali Reza ^a   Ramazani, Ali ^a  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

Author keywords

Heterocycles; Isocyanide; Multicomponent reaction; Passerini reaction; acyloxy carboxamide

Indexed keywords

CYANIDES; DRUG PRODUCTS; REACTION KINETICS;

CARBOXAMIDES; HETEROCYCLES; IN-SITU OXIDATION; ISOCYANIDES; MULTICOMPONENT REACTION; MULTICOMPONENTS; PASSERINI REACTION; SINGLE-STEP; SYNTHETIC APPLICATION; Α-ACYLOXY CARBOXAMIDE;

ALDEHYDES;

EID: 84857777546     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527212799499868     Document Type: Review

References (175)

1. Zhu, J. Multicomponent Reactions, WILEY-VCH: Weinheim, 2005.
2. Dömling, A. Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chem. Rev., 2006, 106, 17-89.
3. Dömling, A.; Ugi, I. Multicomponent reactions with isocyanides. Angew. Chem. Int. Ed., 2000, 39, 3169-3210.
4. Zhu, J. Recent developments in the isonitrile-based multicomponent synthesis of heterocycles. Eur. J. Org. Chem., 2003, 1133-1144.
5. Hulme, C.; Gore, V. "Multi-component reactions: Emerging chemistry in drug discovery" 'From Xylocain to Crixivan'. Curr. Med. Chem., 2003, 10, 51-80.
6. Nair, V.; Rajesh, C.; Vinod, A.U.; Bindu, S.; Sreekanth, A.R.; Mathen, J.S.; Balagopal, L. Strategies for heterocyclic construction via novel multicomponent reactions based on isocyanides and nucleophilic carbenes. Acc. Chem. Res., 2003, 36, 899-907.
7. Mironov, M.A. Design of multi-component reactions: from libraries of compounds to libraries of reactions. QSAR Comb. Sci., 2006, 25, 423-431.
8. Ugi, I.; Werner, B.; Dömling, A. The chemistry of isocyanides, their multicomponent reactions and their libraries. Molecules, 2003, 8, 53-66.
9. Ugi, I. Recent progress in the chemistry of multicomponent reactions. Pure Appl. Chem., 2001, 73, 187-191.
10. Shaabani, A; Maleki, A; Rezayan, A.H.; Sarvary, A. Recent progress of isocyanide-based multicomponent reactions in Iran. Mol. Divers., 2011, 15, 41-68.
11. Dömling, A. The discovery of new isocyanide-based multi-component reactions. Curr. Opin. Chem. Biol., 2000, 4, 318-323.
12. Dömling, A. Recent advances in isocyanide-based multicomponent chemistry. Curr. Opin. Chem. Biol., 2002, 6, 306-313.
13. Simon, C.; Constantieux, T.; Rodriguez, J. Utilisation of 1,3-dicarbonyl derivatives in multicomponent reactions. Eur. J. Org. Chem., 2004, 4957-4980.
14. Liéby-Muller, F.; Simon, C.; Constantieux, T.; Rodriguez, J. Current developments in Michael addition-based multicomponent domino reactions involving 1,3-dicarbonyls and derivatives. QSAR Comb. Sci., 2006, 25, 432-438.
15. Banfi, L.; Riva, R.; Basso, A. Coupling isocyanide-based multicomponent reactions with aliphatic or acyl nucleophilic substitution processes. Synlett, 2010, 23-41.
16. Strecker, A. Ueber die künstliche bildung der milchsäure and einen neuen, dem glycocoll homologen körper. Justus Liebigs Ann. Chem., 1850, 75, 27-45.
17. Ramazani, A.; Ahmadi, Y.; Tarasi, R. Efficient one-pot synthesis of disubstituted 1,3,4-oxadiazole derivatives from the reaction of (Nisocyanimino) triphenylphosphorane, acetaldehyde, a secondary amine, and an electron-poor (E)-cinnamic acid. Heteroat. Chem., 2011, 22, 79-84.
18. Ramazani, A.; Rezaei, A.; Tofangchi Mahyari, A.; Rouhani, M.; Khoobi, M. Three-component reaction of an isocyanide and a dialkyl acetylenedicarboxylate with a phenacyl halide in the presence of water: an efficient method for the one-pot synthesis of γ-iminolactone derivatives. Helv. Chim. Acta, 2010, 93, 2033-2036.
19. Yavari, I.; Khalili, G.; Mirzaei, A. Tandem synthesis of 1-(alkylamino)-2,4- diarylpyrimido[6,1-a]isoquinolin-5-ium chlorides from isoquinoline, Nalkyl benzimidoyl chlorides, and isocyanides. Tetrahedron Lett., 2010, 51, 1190-1192.
20. Esmaeili, A.A.; Hosseinabadi, R.; Habibi, A. An efficient synthesis of highly functionalized 4H-pyrano[3,2-d]isoxazoles via isocyanide-based three-component reaction. Synlett., 2010, 1477-1480.
21. Shaabani, A.; Mofakham, H.; Maleki, A.; Hajishaabanha, F. Novel isocyanide-based one-pot multicomponent syntheses of tetrahydrobenzo[b][1,4]oxazepine and malonamide derivatives. J. Comb. Chem., 2010, 12, 630-632.
22. Yavari, I.; Bayat, M.J.; Sirouspour, M.; Souri, S. One-pot synthesis of highly functionalized 1,2-dihydropyridines from primary alkylamines, alkyl isocyanides, and acetylenic esters. Tetrahedron, 2010, 66, 7995-7999.
23. Teimouri M.B.; Mansouri, F.; Bazhrang, R. Facile synthesis of 1Hpyrazolo[ 1,2-a]pyridazine-5,8-dione derivatives by a one-pot, threecomponent reactions. Tetrahedron, 2010, 66, 259-264.
24. Shaabani, A.; Maleki, A.; Hajishaabanha, F., Mofakham, H.; Seyyedhamzeh, M.; Mahyari, M.; Ng, S.W. Novel syntheses of tetrahydrobenzodiazepines and dihydropyrazines via isocyanide-based multicomponent reactions of diamines. J. Comb. Chem., 2010, 12, 186-190.
25. Shaabani, A.; Soleimani, E.; Sarvary, A.; Rezayan, A.H. A simple and efficient approach to the synthesis of 4H-furo[3,4-b]pyrans via a three-component reaction of isocyanides. Bioorg. Med. Chem. Lett., 2008, 18, 3968-3970.
26. Adib, M.; Sheikhi, E.; Rezaei, N. One-pot synthesis of imidazo[1,2- a]pyridines from benzyl halides or benzyl tosylates, 2-aminopyridines and isocyanides. Tetrahedron Lett., 2011, 52, 3191-3194.
27. Adib, M.; Sheikhi, E.; Kavoosi, A.; Bijanzadeh, H.R. Synthesis of 2-(alkylamino)-5-{alkyl[(2- oxo-2H-chromen-3-yl)carbonyl]amino}-3,4-furandicarboxylates using a multi-component reaction in water. Tetrahedron, 2010, 66, 9263-9269.
28. Yavari, I.; Sabbaghan, M.; Hossaeini, Z.; Reaction between alkyl isocyanides and isopropylidene Meldrum's acid in the presence of bidentate nucleophiles. Mol. Divers., 2007, 11, 1-5.
29. Anary-Abbasinejad, M.; Ghanea, F.; Anaraki-Ardakani, H. One-pot synthesis of highly functionalized stable ketenimines by three-component reaction of cyclohexyl isocyanide, dialkyl acetylenedicarboxylates, and benzoyl hydrazones. Synth. Commun., 2009, 39, 544-551.
30. Ramazani, A.; Tofangchi Mahyari, A.; Rouhani, M.; Rezaei, A. A novel three-component reaction of a secondary amine and a 2-hydroxybenzaldehyde derivative with an isocyanide in the presence of silica gel: an efficient one-pot synthesis of benzo[b]furan derivatives. Tetrahedron Lett., 2009, 50, 5625-5627.
31. Ahmadi, E.; Ramazani, A.; Nekomanesh Haghighi, M. A novel fourcomponent reaction of diethylamine, an aromatic aldehyde and an alkyl isocyanide with dialkyl acetylenedicarboxylates in the presence of silica gel: an efficient route for the regio and stereoselective synthesis of sterically congested alkenes. Tetrahedron Lett., 2007, 48, 5954-5957.
32. Ramazani, A.; Souldozi, A. Iminophosphorane-mediated one-pot synthesis of 1,3,4-oxadiazole derivatives. Arkivoc, 2008, 16, 235-242.
33. Ramazani, A.; Ahmadi, Y.; Rouhani, M.; Shajari, N.; Souldozi, A. The reaction of (N-isocyanimino)triphenylphosphorane with an electron-poor α- haloketone in the presence of aromatic carboxylic acids: A novel threecomponent reaction for the synthesis of disubstituted 1,3,4-oxadiazole derivatives. Heteroat. Chem., 2010, 21, 368-372.
34. Ramazani, A.; Rezaei, A. Novel one-pot, four-component condensation reaction: An efficient approach for the synthesis of 2,5-disubstituted 1,3,4- oxadiazole derivatives by a Ugi-4CR/aza-Wittig sequence. Org. Lett., 2010, 12, 2852-2855.
35. Souldozi, A.; Ramazani, A. The reaction of (Nisocyanimino) triphenylphosphorane with benzoic acid derivatives: a novel synthesis of 2-aryl-1,3,4-oxadiazole derivatives. Tetrahedron Lett., 2007, 48, 1549-1551.
36. Souldozi, A.; Ramazani, A. Bouslimani, N.; Welter, R. The reaction of (Nisocyanimino) triphenylphosphorane with dialkyl acetylenedicarboxylates in the presence of 1,3-diphenyl-1,3-propanedione: a novel three-component reaction for the stereoselective synthesis of dialkyl (Z)-2-(5,7-diphenyl-1,3,4- oxadiazepin-2-yl)-2-butenedioates. Tetrahedron Lett., 2007, 48, 2617-2620.
37. Ramazani, A.; Shajari, N.; Mahyari, A.; Ahmadi, Y. A novel four-component reaction for the synthesis of disubstituted 1,3,4-oxadiazole derivatives. Mol. Divers., 2011, 15, 521-527.
38. Ramazani, A.; Rouhani, M.; Rezaei, A.; Shajari, N.; Souldozi, A. The reaction of (N-isocyanimino)triphenylphosphorane with biacetyl in the presence of aromatic carboxylic acids: efficient one-pot three-component reaction for the synthesis of 3-(5-aryl-1,3,4-oxadiazol-2-yl)-3-hydroxybutan-2-one derivatives. Helv. Chim. Acta, 2011, 94, 282-288.
39. Azizian, J.; Ramazani, A. Haji, M. Synthesis of dialkyl 2-(alkylamino)-4,9- dihydro-9-oxocyclohepta[b]pyran-3,4-dicarboxylates. Helv. Chim. Acta, 2011, 94, 371-375.
40. Sadjadi, S.; Heravi, M.M. Recent application of isocyanides in synthesis of heterocycles. Tetrahedron, 2011, 67, 2707-2752.
41. Heravi, M.M.; Moghimi, S.; Catalytic multicomponent reactions based on isocyanides. J. Iran. Chem. Soc., 2011, 8, 306-373.
42. Ramazani, A.; Rezaei, A.; Mahyari, A.; Rouhani, M.; Khoobi, M.; Yaaghubi, E.; Shabrendi, H.; Vessally, E.; Azizkhani, V.; Amini, I.; Lashgari, H.; Noohi, G.; Shaghaghi, Z.; Sadri, F. Silica gel promotes cascade synthesis of 2-(heteroaryl)acetamide derivatives from isocyanides, dialkylamines, and heteroarylcarbaldehydes. Synth. Commun., 2011, 41, 1444-1454.
43. Ramazani, A.; Mahyari, A.; Three-component reaction of isocyanides and 2-formylbenzoic acid with dibenzylamine catalyzed by silica nanoparticles under solvent-free conditions. Helv. Chim. Acta, 2010, 93, 2203-2209.
44. Ahmadi, E.; Tofangchi Mahyari, A.; Ramazani, A.; Nekomanesh Haghighi, M. A novel three-component reaction of dibenzylamine and an aromatic aldehyde with an alkyl isocyanide in the presence of silica gel: an efficient route for the one-pot synthesis of sterically congested 2-(dibenzylamino)-2-aryl acetamide derivatives. Lett. Org. Chem., 2008, 5, 540-543.
45. Maghsoodlou, M.T.; Marandi, G.; Hazeri, N.; Habibi Khorassani, S.M.; Mirzaei, A.A. Synthesis of 5-aryl-1,3-dimethyl-6-(alkyl or aryl-amino) furo [2,3-d]pyrimidine derivatives by reaction between isocyanides and pyridinecarbaldehydes in the presence of 1,3-dimethylbarbituric acid. Mol. Divers., 2011, 15, 227-231.
46. Marandi, G.; Maghsoodlou, M.T.; Hazeri, N.; Heydari, R.; Habibi Khorassani, S.M.; Ebrahimi, A.; Mollaee Poor, S.; Hosseini Mahdiabad, H.; Nassiri, M.; Kabiri, R. Study of reaction between activated acetylenes and N,N'-diethyl-2-thiobarbituric acid in the presence of isocyanides or triphenylphosphine. Heteroat. Chem., 2010, 21, 228-235.
47. Lieke, W. Ueber das Cyanallyl. Justus Liebigs Ann. Chem., 1859, 112, 316-321.
48. Gautier, A. Ueber die Einwirkung des Chlorwasserstoffs u. a. auf das Aethylund. Justus Liebigs Ann. Chem., 1867, 142, 289-294.
49. Passerini, M.; Simone, L. Sopra gli isonitrili (I). Composto del pisonitrilazobenzolo con acetone ed acido acetico. Gazz. Chim. Ital., 1921, 51, 126-129.
50. Passerini, M. Sopra gli isonitrili(I). Sopra gli isonitrili (II). Composti con aldeidi o con chetoni ed acidi organici monobasici. Gazz. Chim. Ital., 1921, 51, 181-188.
51. Passerini, M.; Ragni, G. Sopra gli isonitrili.- XIX Reazoni con acidi aldehidici e chetonoci. Gazz. Chim. Ital., 1931, 61, 964-969.
52. Moran, E.J.; Tellew, J.E.; Zhao, Z.; Armstrong, R.W. Dehydroamino acidderivatives from D-arabinose and L-serine synthesis of models for the azomycin antitumor antibiotics. J. Org. Chem., 1993, 58, 7848-7859.
53. Banfi, L.; Guanti, G.; Riva, R. Passerini multicomponent reaction of protected α-aminoaldehydes as a tool for combinatorial synthesis of enzyme inhibitors. Chem. Commun., 2000, 985-986.
54. Znabet, A.; Polak, M.M.; Janssen, E.; de Kanter, F.J.J., Turner, N.J.; Orru, R.V.A.; Ruijter, E. A highly efficient synthesis of telaprevir by strategic use of biocatalysis and multicomponent reactions. Chem. Commun., 2010, 46, 7918-7920.
55. Armstrong, R.W.; Tellew, J.E.; Moran, E.J. Stereoselective synthesis of (E) and (Z)-1-azabicyclo[3,1,0]hex-2-ylidene dehydroamino acid-derivatives. J. Org. Chem., 1992, 57, 2208-2211.
56. Otto, H.H.; Schirmeister, T. Cysteine proteases and their inhibitors. Chem. Rev., 1997, 97, 133-171.
57. Semple, J.E.; Rowley, D.C.; Brunck, T.K.; Ripka, W.C. Synthesis and biological activity of P-2-P-4 azapeptidomimetic P-1-argininal and P-1- ketoargininamide derivatives: A novel class of serine protease inhibitors. Bioorg. Med. Chem. Lett., 1997, 7, 315-320.
58. Hulme, C.; Nixey, T. Rapid assembly of molecular diversity via exploitation of isocyanide-based multi-component reactions. Curr. Opin. Drug Disc., 2003, 6, 921-929.
59. Baker, R.H.; Stanonis, D. The Passerini reaction.3. stereochemistry and mechanism. J. Am. Chem. Soc., 1951, 73, 699-702.
60. Maeda, S.; Komagawa, S.; Uchiyama, M.; Morokuma, K. Finding reaction pathways for multicomponent reactions: the Passerini raction is a fourcomponent reaction. Angew. Chem. Int. Ed., 2011, 50, 644-649.
61. Kazemizadeh, A.R.; Ramazani, A. Three component reaction of indane-1,2,3-trione, tosylmethyl isocyanide and benzoic acid derivatives. Arkivoc, 2008, 15, 159-165.
62. Kazemizadeh, A.R.; Ramazani, A. Passerini multicomponent reaction of indane-1,2,3-trione: an efficient route for the one-pot synthesis of sterically congested 2,2-disubstituted indane-1,3-dione derivatives. J. Braz. Chem. Soc., 2009, 20, 309-312.
63. Shoaei, S.M.; Kazemizadeh, A.R.; Ramazani, A. Synthesis and infrered spectra computation of sterically congested 2,2-disubstituted indane-1,3-dione derivatives. Chinese J. Struct. Chem., 2011, 30, 568-574.
64. Kazemizadeh, A.R.; Ramazani, A. Passerini multi-component reaction of indane-1,2,3-trione, isocyanides and 2-furancarboxylic acid. Asian J. Chem., 2011, 23, 4613-4615.
65. Alizadeh, A.; Oskueyan, Q.; Rostamnia, S. Facile and rapid synthesis of α-amidoester derivatives based on the three-component Passerini reaction (P-3CR). Synth. Commun., 2008, 38, 4337-4344.
66. Shabaan, S.; Ba, L.A.; Abbas, M.; Burkholz, T.; Denkert, A.; Gohr, A.; Wessjohann, L.A.; Sasse, F.; Weber, W.; Jacob, C. Multi component reactions for the synthesis of multifunctional agents with activity against cancer cells. Chem. Commun., 2009, 4702-4704.
67. Pirrung, M.C.; Wang, J. Multicomponent reactions of cyclobutanones. J. Org. Chem., 2009, 74, 2958-2963.
68. Hamada, Y.; Shioiri, T. Recent progress of the synthetic studies of biologically active marine cyclic peptides and depsipeptides. Chem. Rev., 2005, 105, 4441-4482.
69. Hamel, E.; Covell, D.G. Antimitotic peptides and depsipeptides. Curr. Med. Chem. Anti Canc. Agents, 2002, 2, 19-53.
70. Paravidino, M.; Scheffelaar, R.; Schmitz, R.F.; de Kanter, F.J.J.; Groen, M.B.; Ruijter, E.; Orru, R.V.A. A flexible six-component reaction to access constrained depsipeptides based on a dihydropyridinone core. J. Org. Chem., 2007, 72, 10239-10242.
71. Baker, R.H.; Schlesinger, A.H. The application of the Passerini reaction to steroid ketones. J. Am. Chem. Soc., 1945, 67, 1499-1500.
72. Jonnalagadda, S.C.; Cruz, J.S.; Connell, R.J.; Scott, P.M.; Mereddy, V.R. Synthesis of α-carboranyl-α-acyloxy-amides as potential BNCT agents. Tetrahedron Lett., 2009, 50, 4314-4317.
73. Al-Tel, T.H.; Al-Qawasmeh, R.A.; Voelter, W. Rapid assembly of polyfunctional structures using a one-pot five and six-component sequential Groebke-Blackburn/Ugi/Passerini process. Eur. J. Org. Chem., 2010, 5586-5593.
74. Azizian, J.; Ramazani, A.; Haji, M. Preparation of α-ketophosphonates derivatives and their application in the synthesis of 1-(N-alkylcarbamoyl)-1- (diethoxyphosphoryl)alkyl benzoates via Passerini reaction. Phosphorus, Sulfur Silicon Relat. Elem., 2011, 186, 326-333.
75. Sieńczyk, M.; Podgórski, D.; Błazejewska, A.; Kulbacka, J.; Saczko, J.; Oleksyszyn, J. Phosphonic pseudopeptides as human neutrophil elastase inhibitors a combinatorial approach. Bioorg. Med. Chem., 2011, 19, 1277-1284.
76. Semple, J.E.; Owens, T.D.; Nguyen, K.; Levy, O.E. New synthetic technology for efficient construction of α-hydroxy-β-amino amides via the Passerini reaction. Org. Lett., 2000, 2, 2769-2772.
77. Carrillo, R.M.; Neo, A.G.; López-García, L.; Marcaccini, S.; Marcos, C.F. Zinc catalysed ester solvolysis. Application to the synthesis of tartronic acid derivatives. Green Chem., 2006, 8, 787-789.
78. Neo, A. G.; Delgado, J.; Polo, C.; Marcaccini, S.; Marcos, C.F. A new synthesis of β-keto amides by reduction of Passerini adducts. Tetrahedron Lett., 2005, 46, 23-26.
79. Yu, H.; Gai, T.; Sun, W.L.; Zhang, M.S. Radical reduction of Passerini 3CR adducts by SmI2/HMPA. Chinese Chem. Lett., 2011, 22, 379-381.
80. Neo, A.G.; Carrillo, R.M.; Delgado, J.; Marcaccini, S.; Marcos, C.F. A multi component approach to the synthesis of 1,3-dicarbonylic compounds. Mol. Divers., 2011, 15, 529-539.
81. Banfi, L.; Guanti, G.; Riva, R.; Basso, A.; Calcagno, E. Short synthesis of protease inhibitors via modified Passerini condensation of N-Boc-α-aminoaldehydes. Tetrahedron Lett., 2002, 43, 4067-4069.
82. Banfi, L.; Basso, A.; Guanti, G.; Riva, R. Passerini reaction- Amine Deprotection-Acyl Migration (PADAM): A convenient strategy for the solid-phase preparation of peptidomimetic compounds. Mol. Divers., 2003, 6, 227-235.
83. Oaksmith, J.M.; Peters, U.; Ganem, B. Three-component condensation leading to β-amino acid diamides: convergent assembly of β-peptide analogues. J. Am. Chem. Soc., 2004, 126, 13606-13607.
84. Bossio, R.; Marcaccini, S.; Pepino, R.; Torroba, T. Study on isocyanides and related compounds: a novel synthetic route to furan derivatives. Synthesis, 1993, 783-785.
85. Beck, B.; Magnin-Lachaux, M.; Herdtweck, E.; Dömling, A. A novel threecomponent butenolide synthesis. Org. Lett., 2001, 3, 2875-2878.
86. Yehia, N.A.M.; Antuch, W.; Beck, B.; Hess, S.; Schauer-Vukašinović, V.; Almstetter, M.; Furer, P.; Herdtweck, E.; Dömling, A. Novel nonpeptidic inhibitors of HIV-1 protease obtained via a new multicomponent chemistry strategy. Bioorg. Med. Chem. Lett., 2004, 14, 3121-3125.
87. Bossio, R.; Marcaccini, S.; Pepino, R. Studies on isocyanides and related compounds synthesis of a novel class of furan derivatives. Liebigs Ann. Chem., 1994, 527-528.
88. Wright, D.L.; Robotham, C.V.; Aboud, K. Studies on the sequential multicomponent coupling/Diels-Alder cycloaddition reaction. Tetrahedron Lett., 2002, 43, 943-946.
89. Fan, L.; Adams, A.N.; Polisar, J.G.; Ganem, B. Studies on the chemistry and reactivity of α-substituted ketones in isonitrile-based multicomponent reactions. J. Org. Chem., 2008, 73, 9720-9726.
90. Sebti, S.; Foucaud, A. A convenient conversion of 2-acyloxy-3- chlorocarboxamides to 3-acyloxy-2-azetidinones in heterogenous media. Synthesis, 1983, 546-549.
91. Marcaccini, S.; Pepino, R.; Marcos, C.F.; Polo, C.; Torroba, T. Studies on isocyanides and related compounds. Synthesis of furan derivatives and their transformation into indole derivatives. J. Heterocycl. Chem., 2000, 37, 1501-1503.
92. Bossio, R.; Marcaccini, S.; Pepino, R. Studies on isocyanides and related compounds. Synthesis of oxazole derivatives via the Passerini reaction. Liebigs Ann. Chem., 1991, 1107-1108.
93. Bossio, R.; Marcaccini, S.; Pepino, R. Studies on isocyanides and related compounds. Synthesis of N-substituted 4-aryl-2-arylthiomethyl oxazole-5- carboxamides. J. Chem. Res. (S), 1991, 320-321.
94. Bossio, R.; Marcaccini, S.; Pepino, R.; Polo, C.; Torroba, T. Synthesis of Nsubstituted 2-alkyl-4-aryloxazole-5-carboxamides. Org. Prep. Proc. Int., 1992, 24, 188-191.
95. Kreye, O.; Westermann, B.; Wessjohann, L.A. A stable convertible isonitrile as a formic acid carbanion [-COOH] equivalent and its application in multicomponent reactions. Synlett, 2007, 3188-3192.
96. He, P.; Wu, J.; Nie, Y.B.; Ding, M.W. New efficient synthesis of 4-aminocarbonyl substituted 4H-3,1-benzoxazines by a Passerini 3CC/Staudinger/aza-Wittig sequence. Tetrahedron Lett., 2009, 65, 8563-8570.
97. Falck, J.R.; Manna, S. An intramolecular Passerini reaction: Synthesis of hydrastine. Tetrahedron Lett., 1981, 22, 619-620.
98. Kreye, O.; Tóth, T.; Meier, M.A.R. Introducing multicomponent reactions to polymer science: Passerini reactions of renewable monomers. J. Am. Chem. Soc., 2011, 133, 1790-1792.
99. Owens, T.D.; Araldi, G.L.; Nutt, R.F.; Semple, J.E. Concise total synthesis of the prolyl endopeptidase inhibitor eurystatin A via a novel Passerini reaction-deprotection-acyl migration strategy. Tetrahedron Lett., 2001, 42, 6271-6274.
100. Owens, T.D.; Semple, J.E. Atom-economical synthesis of the N(10)-C(17) fragment of cyclotheonamides via a novel Passerini reaction-deprotectionacyl migration strategy. Org. Lett., 2001, 3, 3301-3304.
101. Faure S.; Hjelmgaard, T.; Roche, S.P.; Aitken, D.J. Passerini reaction-amine deprotection-acyl migration peptide assembly: Efficient formal synthesis of cyclotheonamide C. Org. Lett., 2009, 11, 1167-1170.
102. Beck, B.; Larbig, G.; Mejat, B.; Magnin-Lachaux, M.; Picard, A.; Herdtweck, E.; Dömling, A. Short and diverse route toward complex natural product-like macrocycles. Org. Lett., 2003, 5, 1047-1050.
103. Leon, F.; Rivera, D.G.; Wessjohann, L.A. Multiple multicomponent macrocyclizations including bifunctional building blocks (MiBs) based on Staudinger and Passerini three-component reactions. J. Org. Chem., 2008, 73, 1762-1767.
104. Zakrzewski, J.; Jezierska, J.; Hupko, J. 4-Isocyano-2,2,6,6- tetramethylpiperidin-1-oxyl: A valuable precursor for the synthesis of new nitroxides. Org. Lett., 2004, 6, 695-697.
105. Soeta, T.; Kojima, Y.; Ukaji, Y.; Inomata, K. Borinic acid catalyzed α-addition to isocyanide with aldehyde and water. Tetrahedron Lett., 2011, 52, 2557-2559.
106. Rubinshtein, M.; James, C.R.; Young, J.L.; Ma, Y.J.; Kobayashi, Y.; Gianneschi, N.C.; Yang, J. Facile procedure for generating side chain functionalized poly(α-hydroxy acid) copolymers from aldehydes via a versatile Passerini type condensation. Org. Lett., 2010, 12, 3560-3563.
107. Ugi, I.; Meyr, R. Isonitrilr 5. Erweiterter anwendungsbereich der Passerini reaktion. Chem. Ber., 1961, 94, 2229-2233.
108. Nixey, T.; Hulme, C. Rapid generation of cis-constrained norstatine analogs using a TMSN3- modified Passerini MCC/N-capping strategy classical Passerini reactions. Tetrahedron Lett., 2002, 43, 6833-6835.
109. Yue, T.; Wang, M. X.; Wang, D. X.; Zhu, J. Asymmetric synthesis of 5-(1- hydroxyalkyl)tetrazoles by catalytic enantioselective Passerini-type reactions. Angew. Chem. Int. Ed., 2008, 47, 9454-9457.
110. Soeta, T.; Kojima, Y.; Ukaji, Y.; Inomata, K. O-Silylative Passerini reaction: A new one-pot synthesis of α-siloxyamides. Org. Lett., 2010, 12, 4341-4343.
111. Sutherland, J.D.; Mullen, L.B.; Buchet, F.F. Potentially prebiotic Passerinitype reactions of phosphates. Synthesis, 2008, 2161-2163.
112. Henkel, B.; Beck, B.; Westner, B.; Mejat, B.; Dömling, A. Convergent multicomponent assembly of 2-acyloxymethyl thiazoles. Tetrahedron Lett., 2003, 44, 8947-8950.
113. El Kaim, L.; Gizolme, M.; Grimaud, L. O-Arylative Passerini reactions. Org. Lett. 2006, 8, 5021-5023.
114. El Kaim, L.; Gizolme, M.; Grimaud, L.; Oble, J. Smiles rearrangements in Ugi and Passerini-type couplings: new multicomponent access to O- and Narylamides. J. Org. Chem., 2007, 72, 4169-4180.
115. Barthelon, A.; El Kaïm, L.; Gizolme, M.; Grimaud, L. Thiols in Ugi and Passerini-Smiles-type couplings. Eur. J. Org. Chem., 2008, 5974-5987.
116. Müller, E.; Zeeh, B. Lewissäure-katalysierte umsetzung von aliphatischen ketonen mit tert-butyl isonitril. Justus Liebigs Ann. Chem., 1968, 715, 47-51.
117. Müller, E.; Zeeh, B. Lewissäure-katalysierte umsetzung von carbonylverbindungen mit tert-butyl isonitril. Justus Liebigs Ann. Chem., 1966, 696, 72-80.
118. Saegusa, T.; Taka-ishi, N.; Fujii, H. Reaction of carbonyl compound with isocyanide. Tetrahedron, 1968, 24, 3795-3798.
119. Schiess, M.; Seebach, D. N-methyl-C-(trichlorotitanio)formimidoyl chloride, a highly efficient reagent for homologations of aldehydes and ketones to α-hydroxycarboxamides. Helv. Chim. Acta, 1983, 66, 1618-1623.
120. Seebach, D.; Adam, G.; Gees, T.; Schieae, M.; Wiegand, W. Scope and limitations of the TiCl4-mediated additions of isocyanides to aldehydes and ketones with formation of α-hydroxycarboxylic acid-amides. Chem. Ber., 1988, 121, 507-517.
121. Seebach, D.; Beck, A. K.; Schieae, M.; Widler, L.; Woycott, A. Some recent advances in the use of titanium reagents for organic synthesis. Pure Appl. Chem., 1983, 55, 1807-1822.
122. Carofiglio, T.; Cozzi, P.G.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Nonorganometallic pathway of the Passerini reaction assisted by titanium tetrachloride. Organometallics, 1993, 12, 2726-2736.
123. Carofiglio, T.; Floriani, C. Nonorganometallic pathway of the Passerinl reaction assisted by TiCl4. Organometallics, 1991, 10, 1659-1660.
124. Kalinski, C.; Lemoine, H.; Schmidt, J.; Burdack, C.; Kolb, J.; Umkehrer, M.; Ross, G. Multicomponent reactions as a powerful tool for generic drug synthesis. Synthesis, 2008, 4007-4011.
125. Lamberth, C.; Jeanguenat, A.; Cederbaum, F.; Mesmaeker, A.D.; Zeller, M.; Kempf, H.J. Zeun, R. Multicomponent reactions in fungicide research: the discovery of mandipropamid. Bioorg. Med. Chem., 2008, 16, 1531-1545.
126. Xia, Q.; Ganem, B. Metal-mediated variants of the Passerini reaction: a new synthesis of 4-cyanooxazoles. Synthesis, 2002, 1969-1972.
127. Xia, Q.; Ganem, B. Metal-promoted variants of the Passerini reaction leading to functionalized heterocycles. Org. Lett., 2002, 4, 1631-1634.
128. Kern, O.; Motherwell, W.B. A novel isocyanide based three component reaction. Chem. Commun., 2003, 2988-2989.
129. Masdeu, C.; Gómez, E.; Williams, N.A.; Lavilla, R. Hydro-, halo and seleno carbamoylation of cyclic enol ethers and dihydropyridines: new mechanistic pathways for Passerini and Ugi-type multicomponent reactions. QSAR Comb. Sci., 2006, 25, 465-473.
130. Krishna, P.R.; Lopinti, K. Diastereoselective Passerini reaction of chiral 2,3- epoxy aldehydes with TosMIC. Synlett., 2007, 83-86.
131. Umbreen, S.; Brockhaus, M.; Ehrenberg, H.; Schmidt, B. Norstatines from aldehydes by sequential organocatalytic α-amination and Passerini reaction. Eur. J. Org. Chem., 2006, 4585-4595.
132. Krishna, P.R.; Dayakar, G.; Reddy, P.V.N. Diastereoselective Passerini reactions using p-toluenesulfonylmethyl isocyanide (TosMIC) as the isonitrile component. Tetrahedron Lett., 2006, 47, 5977-5980
133. Qu, W.; Zha, Z.; Ploessl, K.; Lieberman, B.P.; Zhu, L.; Wise, D.R.; Thompson, C.B.; Kung, H.F. Synthesis of optically pure 4-fluoro-glutamines as potential metabolic imaging agents for tumors. J. Am. Chem. Soc., 2011, 133, 1122-1133.
134. Frey, R.; Galbraith, S.G.; Guelfi, S.; Lamberth, C.; Zeller, M. First examples of a highly stereoselective Passerini reaction: a new access to enantiopure mandelamides. Synlett, 2003, 1536-1538.
135. Bock, H.; Ugi, I. Multicomponent reactions.2. Stereoselective synthesis of 1(S)-camphor-2-cis-methylidene-isocyanide and its application in Passeriniand Ugi-reaction. J. Prakt. Chem., 1997, 339, 385-389.
136. Ziegler, T.; Kaisers, H.J.; Schlömer, R.; Koch, C. Passerini and Ugi reactions of benzyl and acetyl protected isocyanoglucoses. Tetrahedron, 1999, 55, 8397-8408.
137. Ziegler, T.; Schlömer, R.; Koch, C. Passerini and Ugi reactions of anomeric glucosyl isonitriles. Tetrahedron Lett., 1998, 39, 5957-5960.
138. Grenouillat, N.; Vauzeilles, B.; Beau, J.M. Lipid analogs of the nodulation factor using the Ugi/Passerini multicomponent reactions: preliminary studies on the carbohydrate monomer. Heterocycles, 2007, 73, 891-901.
139. Bergemann, M.; Neidlein, R. Studies on the reactivity of α-cyano-α- isocyanoalkanoates-versatile synthons for the assembly of imidazoles. Helv. Chim. Acta, 1999, 82, 909-918.
140. Berłozecki, S.; Szymanski, W.; Ostaszewski, R. α-Amino acids as acid components in the Passerini reaction: influence of N-protection on the yield and stereoselectivity. Tetrahedron, 2008, 64, 9780-9783.
141. Gulevich, A.V.; Shpilevaya, I.V.; Nenajdenko, V.G. The Passerini reaction with CF3-carbonyl compounds-multicomponent approach to trifluoromethyl depsipeptides. Eur. J. Org. Chem., 2009, 3801-3808.
142. Denmark, S.E.; Wynn, T. Lewis base activation of Lewis acids: Catalytic enantioselective allylation and propargylation of aldehydes. J. Am. Chem. Soc., 2001, 123, 6199-6200.
143. Denmark, S.E.; Fan, Y. The first catalytic, asymmetric alpha-additions of isocyanides. Lewis-base-catalyzed, enantioselective Passerini-type reactions. J. Am. Chem. Soc., 2003, 125, 7825-7827.
144. Denmark, S.E.; Fan, Y. Catalytic, enantioselective α-additions of isocyanides: Lewis base catalyzed Passerini-type reactions. J. Org. Chem., 2005, 70, 9667-9676.
145. Wang, S.; Wang, M.X.; Wang, D.X.; Zhu, J. Asymmetric Lewis acid catalyzed addition of isocyanides to aldehydes. Synthesis of 5-amino-2-(1-hydroxyalkyl)oxazoles. Eur. J. Org. Chem., 2007, 4076-4080.
146. Yue, T.; Wang, M.X.; Wang, D.X.; Masson, G.; Zhu, J. Catalytic asymmetric Passerini-type reaction: chiral aluminum-organophosphate-catalyzed enantioselective α-addition of isocyanides to aldehydes. J. Org. Chem., 2009, 74, 8396-8399.
147. Kusebauch, U.; Beck, B.; Messer, K.; Herdtweck, E.; Dömling, A. Massive parallel catalyst screening: toward asymmetric MCRs. Org. Lett., 2003, 5, 4021-4024.
148. Andreana, P.R.; Liu, C.C.; Schreiber, S.L. Stereochemical control of the Passerini reaction. Org. Lett., 2004, 6, 4231-4233.
149. Wang, S.X.; Wang, M.X.; Wang, D.X.; Zhu, J. Catalytic enantioselective Passerini three-component reaction. Angew. Chem. Int. Ed., 2008, 47, 388-391.
150. Szymanski, W.; Zwolinska, M.; Ostaszewski, R. Studies on the application of the Passerini reaction and enzymatic procedures to the synthesis of tripeptide mimetics. Tetrahedron, 2007, 63, 7647-7653.
151. Szymanski, W.; Ostaszewski, R. Toward stereocontrolled, chemoenzymatic synthesis of unnatural peptides. Tetrahedron, 2008, 64, 3197-3203.
152. Ostaszewski, R.; Portlock, D.E.; Fryszkowska, A.; Jeziorska, K. Combination of enzymatic procedures with multicomponent condensations. Pure Appl. Chem., 2003, 75, 413-419.
153. Szymanski, W.; Ostaszewski, R. Multicomponent diversity and enzymatic enantioselectivity as a route towards both enantiomers of α-amino acids-a model study. Tetrahedron: Asymmetry, 2006, 17, 2667-2671.
154. Ngouansavanh, T.; Zhu, J. Alcohols in isonitrile-based multicomponent reaction: Passerini reaction of alcohols in the presence of O-iodoxybenzoic acid. Angew. Chem. Int. Ed., 2006, 45, 3495-3497.
155. de Moliner, F.; Crosignani, S.; Banfi, L.; Riva, R.; Basso, A. Synthesis of 5-carboxamide-oxazolines with a Passerini-Zhu/Staudinger-Aza-Wittig twostep protocol. J. Comb. Chem., 2010, 12, 613-616.
156. Brioche, J.; Masson, G.; Zhu, J. Passerini three-component reaction of alcohols under catalytic aerobic oxidative conditions. Org. Lett., 2010, 12, 1432-1435.
157. Henze, M.; Kreye, O.; Brauch, S.; Nitsche, C.; Naumann, K.; Wessjohann, L.A.; Westermann, B. Photoaffinity-labeled peptoids and depsipeptides by multicomponent reactions. Synthesis, 2010, 2997-3003.
158. Shapiro, N.; Vigalok, A. Highly efficient organic reactions "on water", "in water", and Both. Angew. Chem. Int. Ed., 2008, 47, 2849-2852.
159. Cai, X. Direct Passerini reaction of aldehydes, isocyanides, and aliphatic alcohols catalyzed by bismuth (III) triflate. Int. J. Chem., 2011, 3, 216-219.
160. Yanai, H.; Oguchi, T.; Taguchi, T. Direct alkylative Passerini reaction of aldehydes, isocyanides, and free aliphatic alcohols catalyzed by indium (III) triflate. J. Org. Chem., 2009, 74, 3927-3929.
161. Zhang, X.Y.; Li, Y.Z.; Fan, X.S.; Qu, G.R.; Wang, J.J.; Hu, X.Y. Ionic liquid [bmim][BF4] as a green medium for Passerini reaction. Chinese Chem. Lett., 2006, 17, 578-580.
162. Andrade, C.K.Z.; Takada, S.C.S.; Suarez, P.A.Z.; Alves, M.B. Revisiting the Passerini reaction under eco-friendly reaction conditions. Synlett, 2006, 1539-1542.
163. Fan, X.; Li, Y.; Zhang, X.; Qu, G.; Wang, J. A novel and green version of the Passerini reaction in an ionic liquid ([bmim][BF4]). Can. J. Chem., 2006, 84, 794-799.
164. Koszelewski, D.; Szymanski, W.; Krysiak, J.; Ostaszewski, R. Solvent-free Passerini reactions. Synth. Commun., 2008, 38, 1120-1127.
165. Basso, A.; Banfi, L.; Riva, R.; Piaggio, P.; Guanti, G. Solid-phase synthesis of modified oligopeptides via Passerini multicomponent reaction. Tetrahedron Lett., 2003, 44, 2367-2370.
166. Barreto, A.F.S.; Vercillo, O.E.; Andrade, C.K.Z. Microwave-assisted Passerini reactions under solvent-free conditions., J. Braz. Chem. Soc., 2011, 22, 462-467.
167. Jenner, G. Effect of high pressure on sterically congested Passerini reactions. Tetrahedron Lett., 2002, 43, 1235-1238.
168. Jenner, G.; Bacem, B. High pressure effect on organic reactions in fluorophobic media. J. Phys. Org. Chem., 2003, 16, 265-270.
169. Mironov, M.A.; Ivantsova, M.N.; Tokareva, M.I.; Mokrushin, V.S. Acceleration of the Passerini reaction in the presence of nucleophilic additives. Tetrahedron Lett., 2005, 46, 3957-3960.
170. Pirrung, M.C.; Sarma, K.D. Aqueous medium effects on multi-component reactions. Tetrahedron, 2005, 61, 11456-11472.
171. Extance, A.R.; Benzies, D.W.M.; Morrish, J.J. Production of small libraries optimising and examining the scope of aqueous acceleration of the Passerini reaction. QSAR Comb. Sci., 2006, 25, 484-490.
172. Pirrung, M.C.; Sarma, K.D. Multicomponent reactions are accelerated in water. J. Am. Chem. Soc., 2004, 126, 444-445.
173. Pirrung, M.C.; Sarma, K.D.; Wang, J. Hydrophobicity and mixing effects on select heterogeneous, water-accelerated synthetic reactions. J. Org. Chem., 2008, 73, 8723-8730.
174. Dai, W.M.; Li, H.M. Lewis acid-catalyzed formation of Ugi four-component reaction product from Passerini three-component reaction system without an added amine. Tetrahedron, 2007, 63, 12866-12876.
175. Okandeji, B.O.; Sello, J.K. Brønsted acidity of substrates influences the outcome of Passerini three-component reactions. J. Org. Chem., 2009, 74, 5067-5070.