Recent progress in the synthesis and applications of heterocycles derived from enaminonitriles

Current Organic Chemistry

Volumn 15, Issue 5, 2011, Pages 753-781

  Bondock, Samir ^a   Tarhoni, Abd El Gaber ^a   Fadda, Ahmed A ^a  

^a Mansoura University   (Egypt)

Author keywords

C nucleophiles; Dimethylformamide dimethylacetal; Enaminonitriles; Heterocycles; N nucleophiles; Synthesis

Indexed keywords

CONDENSATION REACTIONS; DIMETHYLFORMAMIDE; NUCLEOPHILES;

BUILDING BLOCKES; C-NUCLEOPHILE; DIMETHYLFORMAMIDE-DIMETHYLACETAL; ENAMINONITRILE; HETEROCYCLES; HETEROCYCLIC COMPOUND; N-NUCLEOPHILE; RECENT PROGRESS; SYNTHETIC ROUTES;

SYNTHESIS (CHEMICAL);

EID: 79951712195     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527211794519041     Document Type: Article

References (146)

1. Madkour, H. M. F.; Afify, A. A. E.; Abdalha, A. A.; Elsayed, G. A., Salem, M.S. Synthetic utility of enaminonitrile moiety in heterocyclic synthesis: Synthesis of some new thienopyrimidine. Phosphorus Sulfur Silicon Rel. Elem., 2009, 184, 719-732.
2. Shaaban, M. R.; Saleh, T. S.; Farag, A. M. Synthesis and antimicrobial evaluation of new thiophene and 1,3,4-thiadiazole derivatives. Heterocycles, 2009, 78, 151-159.
3. Elkholy, A.; Al-Qalaf, F.; Elnagdi, M. H. Regio-orientation in condensation of aminopyrazoles with 1,3-difunctional reagents: synthesis of new pyrazolo[ 1,5-a]pyrimidines; pyrazolo[3,4-d]pyridazines and 2,4-dihydropyrano [2,3-c]pyrazoles. Arkivoc, 2008, xiv, 124-131.
4. Salaheldin, A. M.; Oliveira-Campos, A. M. F.; Rodrigues, L. M. 3- Aminopyrroles and their application in the synthesis of pyrrolo[3,2- d]pyrimidine (9-deazapurine) derivatives. Arkivoc, 2008, xiv, 180-190.
5. Madkour, H. M. F.; Afify, A. A. E.; Elsayed, G. A.; Salem M.S. Synthetic utility of enaminonitrile moiety in heterocyclic synthesis. Bulg. Chem. Comm., 2008, 40, 147-159.
6. Azab, M. E. Utility of the enaminonitrile moiety in the synthesis of some biologically active thienopyrimidine derivatives. Phosphorus Sulfur Silicon Rel. Elem., 2008, 183, 1766-1782.
7. Dyachenko, V. D.; Dyachenko, A. D. Synthesis of 4-alkyl(aryl, hetaryl)-2- thioxo-5,6,7,8-tetrahydroquinoline-3-carbonitriles and their derivatives by cross-recyclization of 4-alkyl(aryl,hetaryl)-2,6-diamino-4H-thiopyran-3,5- dicarbonitriles with 4-(cyclohex-1-en-1-yl)-morpholine, alkyl halides, and cyclohexanone. Russ. J. Org. Chem., 2008, 44, 412-420.
8. Kobayashi, K.; Hashimoto, K.; Ukon, T.; Fukamachi, S.; Morikawa, O.; Konishi, H. Synthesis of 1-aminonaphthalene-2-carbonitrile derivatives by the reaction of 2-vinylbenzonitriles with 2-lithioacetonitrile. Synthesis 2008, 584-588.
9. Mulwad, V. V.; Mayekar, S. A. Synthesis and antimicrobial screening of 5-(4, 7-dimethyl-2-oxo-2H-benzopyran-6-ylazo)-2-methyl-6-morpholin-4-yl-2,3- dihydro-3H-pyrimidin-4-one and 5-(4,7-dimethyl-2-oxo-2H-benzopyran-6- ylazo)-2-methyl-6-piperidin-1-yl-2,3-dihydro-3H-pyrimidin-4-one. Indian J. Chem. Sect. B, 2007, 46, 1873-1878.
10. Hassaneen, H. M. E.; Awad, E. M.; Hassaneen, H. A. Studies with 6,7- dimethoxy-3,4-dihydroisoquinolin-1-yl-acetonitrile: Novel syntheses of 1- azolyl- And pyridoisoquinolines. Z. Naturforsch., 2007, 62, 111-116.
11. El-Sayed, N. A.; Farag, A. E.; El-Saadi, M. T. Synthesis and antiinflammatory activity of some fused pyrimidines. Bull. Pharm. Sci. 2006, 29, 520-546.
12. Salgado-Zamora, H.; Taylor, E. C. Synthesis of enaminonitrile imidazo[1,2- a]pyridine by an Ehrlich-Sachs type reaction on 2-nitrosopyridine. Heterocycl. Commun., 2006, 12, 307-312.
13. Al-Saleh, B.; Makhseed, S.; Hassaneen, H. M. E.; Elnagdi, M. H. Studies with functionally substituted enamines: The reactivity of enaminals and enamino esters toward naphthoquinone, hydrazonoyl halides, aminoazoles and hippuric acid. Synthesis 2006, 59-62.
14. Macho, S.; Miguel, D.; Neo, A. G.; Rodriguez, T.; Torroba, T. Cyclopentathiadiazines, new heterocyclic materials from cyclic enaminonitriles. Chem. Commun., 2005, 334-336.
15. Elghamry, I. Cyclotrimerization of enaminones: An efficient method for the synthesis of 1,3,5-triaroylbenzenes. Synthesis 2003, 2301-2303.
16. Volochnyuk, D. M.; Kostyuk, A. N.; Sibgatulin, D. A.; Chernega, A. N. Synthesis of functionalized m-bistrifluoromethylbenzenes via cyclocondensation of 1,1,1,5,5,5-hexafluoroacetylacetone with enamines. Tetrahedron, 2005, 61, 2839-2847.
17. Al-Omran, A. Z. A.; Elassar, A.; El-Kair, A. Synthesis of condensed heteroaromatics: Novel synthesis of aminoquinolizinone derivatives as anti-HIV agents. Tetrahedron, 2001, 57, 10163-10170.
18. Erian, A. W. The chemistry of ń-enaminonitriles as versatile reagents in heterocyclic synthesis. Chem. Rev., 1993, 93, 1991-2005.
19. Al-Azmi, A.; Elassar, A.-Z. A.; Booth, B. L. The chemistry of diaminomaleonitrile and its utility in heterocyclic synthesis. Tetrahedron, 2003, 59, 2749-2763.
20. Wamhoff, H.; Dzeni, J.; Hirota, K. Uracils: Versatile starting materials in heterocyclic synthesis. Adv. Heterocyl. Chem., 1992, 55, 129-259.
21. Patai, S. The Chemistry of Enamines, J. Wiley and Sons, New York, 1994.
22. Lue, P.; Greenhill, J. V. Enaminones in heterocyclic synthesis. Adv. Heterocyl. Chem., 1996, 67, 207-343.
23. Ferraz, H. M. C.; Goncalo, E. R. S. Recent preparations and synthetic applications of enaminones. Quim. Nova, 2007, 30, 957-964.
24. Elassar, A.; El-Kair, A. Recent developments in the chemistry of enaminones. Tetrahedron, 2003, 59, 8463-8480.
25. Nergi, G.; Kascheres, C.; Kascheres, A. J. Recent development in preparation reactivity and biological activity of enaminoketones and enaminothiones and their utilization to prepare heterocyclic compounds. J. Heterocycl. Chem., 2004, 41, 461-491.
26. Riyadh, S. M.; Abd-Elhamid, I. A.; Al-Matar, H. M.; Hilmy, N. M.; Elnagdi, M. H. Enamine as precursors to polyfunctional heteroaromatic compounds; a decade of development. Heterocycles, 2008, 75, 1849-1905.
27. Stanovnik, B. The synthesis of 2-substituted 3-dimethylaminopropenoates and related compounds and their application to the synthesis of heterocyclic synthesis. Molecules, 1997, 1, 123-127.
28. Stanovnik, B. 2-Substituted 3-dimethylamino- and -3-cyanopropenoates in the synthesis of heterocyclic systems. J. Heterocycl. Chem., 1999, 36, 1581-1593.
29. Erian, A. W.; Sherif, S. M.; Mohamed, N. R. Heterocyclic synthesis with activated nitriles: An expeditus synthetic approach to polyfunctionally substituted pyrroles, heterocyclopyrimidines and coumarins. Arkivoc, 2001, x, 85-94.
30. Duaza, J. P.; Church, R. F. β-[(Dialkylamino)methylene]-ń-oxonitriles. US Patent, 5, 059, 709 (C1. 558-309;C07C253/00), 1991; Chem. Abstr., 1992, 116, 83392s.
31. Shaaban, M. R. Synthesis and antimicrobial evaluation of novel pyrazolo[ 1,5-a]pyrimidine, pyrimido[1,2-a]benzimidazole, triazolo[4,3- a]pyrimidine and pyrido[1,2-a]benzimidazole derivatives incorporated phenylsulfonyl moiety. Heterocycles, 2008, 75, 3005-3014.
32. Farag, A. M.; Dawood, K. M.; Elmenoufy, H. A. A convenient route to pyridones, pyrazolo[2,3-a]pyrimidines and pyrazolo[5,1-c]triazines incorporating antipyrine moiety. Heteroatom Chem., 2004, 15, 508-514.
33. Radwan, M. A. A.; El-Sherbiny, M. Synthesis and antitumor activity of indolylpyrimidines: Marine natural product meridianin D analogues. Bioorg. Med. Chem., 2007, 15, 1206-1211.
34. Dawood, K. M.; Farag, A. M.; Kandeel, Z. E. Heterocyclic synthesis via enaminonitriles: One-pot synthesis of some new pyrazole, isoxazole, pyrimidine, pyrazolo[1,5-a]pyrimidine, pyrimido[1,2-a]benzimidazole and pyrido[1,2-a]benzimidazole derivatives. J. Chem. Res. (S), 1999, 88-89.
35. Dawood, K. M.; Kandeel, Z. E.; Farag, A. M. Heterocyclic Synthesis via Enaminonitriles: A convenient route to some new pyrazole, isoxazole, pyrimidine, Pyrazolo[1,5-a]pyrimidine, Pyrimido[1,2-a]benzimidazole and Pyrido[1,2-a]benzimidazole derivatives. J. Chem. Res. (S), 1998, 208-209.
36. Ibrahim, H. M.; Makhseed, S.; Abdel-Motaleb, R. M.; Makhlouf, A.-M. A.- S; Elnagdi, M. H. Utility of cyanoacetamides as precursors to pyrazolo[3,4- d]pyrimidin-4-ones, 2-aryl-6-substituted 1,2,3-triazolo[4,5-d]pyrimidines and pyrazolo[1,5-a]pyrimidine-3-carboxamides. Heterocycles, 2007, 71, 1951-1966.
37. Al-Omran, F.; El-Khair, A. A.; Elnagdi, M. H. Studies with Polyfunctionally Substituted Heteroaromatics: A novel synthesis of substituted 4,8-Diaminoisoquinolines as potential antiparasitic agents. J. Chem. Res. (S), 1998, 798-799.
38. Al-Omran, F. Studies with 1-functionally substituted alkylbenzotriazoles: An efficient route for the synthesis of 1-azolylbenzotriazoles, benzotriazolylazines and benzotriazolylazoloazines. J. Heterocycl. Chem., 2000, 37, 1219-1223.
39. Abdallah, S. O.; Metwally, N. H.; Anwar, H. F.; Elnagdi, M. H. Synthesis and chemical reactivity of 3-oxo-2-arylhydrazono-propanenitriles. J. Heterocycl. Chem., 2005, 42, 781-786.
40. Al-Matar, H. M.; Riyadh, S. M.; Elnagdi, M. H. 2-Arylhydrazononitriles in heterocyclic synthesis: A novel route to 1,3-diaryl-1,2,4-triazol-5-amines via a Tiemann rearrangement of arylhydrazonoamidoximes. Arkivoc, 2007, xiii, 53-62.
41. Wolfbeis, O. S. One pot synthesis of 3-amino-1H-pyrazole-4-carbonitrile. Monatsh. Chem., 1981, 112, 875-877.
42. Mohareb, R. M.; Sherif, S. M. Heterocyclic syntheses with isothiocyanates: a novel synthetic approach to polyfunctionally substituted pyrazoles and their fused derivatives. Sulfur Lett., 1992, 15, 91-101
43. Bondock, S.; Tarhouni, A.; Fadda, A. A. Utility of cyanoacetic acid hydrazide in heterocyclic synthesis. Arkivoc. 2006, ix, 113-156.
44. Hassaneen, H. M.; Harhash, A. H. E.; Abounada, N. M.; Abdallah, T. A.; Algharib, M. S. Cyano(1-methylbenzimidazol-2-yl)thioacetanilide in the synthesis of 2,3-dihydro-1,3,4-thiadiazole derivatives. J. Chem. Res. (S), 1993, 194-195.
45. 4- thiazoline and thiazolidinone derivatives. Arch. Pharmazie 1991, 324, 469-471.
46. Krey, P.; Dehne, H. Reactivity and biological activity in the thiazole series, Part 4. Pharmazie, 1981, 36, 518-519.
47. Shoukry, M. M.; Mahgoub, A. E. S.; Elnagdi, M. H. Metal chelates of pyridine- 2-ylthioureas. J. Inorg. Nucl. Chem., 1980, 42, 1171-1176.
48. Mohareb, R. M.; Shams, H. Z.; Aziz, S. I. Novel synthesis of 4-(coumarin-3- yl)-1,3-thiazole, 2-(coumarin-3-carbonyl)thieno[2,3-b]pyridine, and 2- (coumarin-3-carbonyl)thiophene derivatives. J. Chem. Res. (S), 1992, 154-155.
49. Ammar, Y. A.; Aly, M. M.; Al-Sehemi, A. G.; Mohamed, Y. A.; Salem, M. A.; El-Gaby, M. S. A. Cyanoacetanilides intermediates in heterocyclic synthesis. Part 4: Preparation of some hitherto unknown thiazolidine and bisthi azolidine derivatives. Phosphorus Sulfur Silicon Rel. Elem., 2008, 183, 1710-1721.
50. Bondock, S.; Rabie, R.; Etman, H. A.; Fadda, A. A. Synthesis and antimicrobial activity of some new heterocycles incorporating antipyrine moiety. Eur. J. Med. Chem., 2008, 43, 2122-2129.
51. Elgemeie, G. H; Widyan, K.; Kurz, T. Novel synthesis of fluorinated cyanoketene N,S-acetals and their conversions to fluorinated pyrazole derivatives. Phosphorus Sulfur Silicon Rel. Elem., 2006, 181, 299-304.
52. Gewald, K.; Schindler, R. Cyclisierungen mit cyanthioacetamid in gegenwart von schwefel. J. Prakt. Chem., 1990, 332, 223-228.
53. Gewald, K.; Hain, U. Preparation of 2-alkoxy-5-amino-4-phenylthieno[2,3- d]pyrimidines. Ger. Patent, DD, 273, 441, 1989; Chem. Abstr., 1990, 113, 115332d.
54. Sherif, S. M.; Wardakhan, W. W.; Mohareb, R. M. β-Enaminonitriles in Heterocyclic Synthesis: A Novel One-pot Synthesis of Thiophenes and their Fused Derivatives. J. Chem. Res. (S), 1996, 356-357.
55. Khalil, K. D.; Al-Matar, H. M.; Al-Dorri, D. M.; Elnagdi, M. H. Studies with enaminones and enaminonitriles: synthesis of 3-aroyl and 3-heteroaroylpyrazolo-[ 1,5-a]pyrimidines. Tetrahedron, 2009, 65, 9421-9427.
56. Augustin, M.; Jahreis, M.; Rudolf, D. Synthese offenkettiger und cyclischer ketenheteroacetale aus ungesaettigten β-ketonitrilen. Synthesis, 1977, 472-474.
57. Braeuniger, H.; Peseke, K.; Bauch, M.; Rohde, M.; Tech, B. Preparation and reactions of [bis(methylthio)methylene]cyanoacetanilides. Naturwiss. Reihe 1984, 33, 53-61; Chem. Abstr., 1987, 106, 138322v.
58. Erian, A. W.; Sherief, S. M. The chemistry of thiocyanic esters. Tetrahedron, 1999, 55, 7957-8024.
59. Elnagdi, M. H.; Fahmy, S. M.; Hafez, E. A.-A.; Elmoghayar, M. R. H.; Amer, S. A. R. Pyrimidine derivatives and related compounds. A novel synthesis of pyrimidines, pyrazolo[4,3-d]pyrimidines and isoxazolo[4,3- d]pyrimidine. J. Heterocycl. Chem., 1979, 16, 1109-1111.
60. Nawwar, G. A. M.; Osman, S. A.; El-Bayanki, K. A. M.; Elgemeie, G. E. H.; Elnagdi, M. H. Nitroles in heterocyclic synthesis: New routes for synthesis of pyran, pyridine and pyrrole derivatives. Heterocycles 1985, 23, 2983-2988.
61. Sadek, K. U.; El-Maghraby, M. A.; Selim, M. A.; Elnagdi, M. H. Activated nitriles in heterocyclic synthesis. Synthesis of pyrimidine derivatives. Bull. Chem. Soc. Jpn., 1988, 61, 539-541.
62. Elnagdi, M. H. Reactions with β-cyanoethylhydrazine-I. A route for the preparation of pyrazolo[1,5-a]pyrimidines and pyrrolo[1,2-b]pyrrazoles. Tetrahedron, 1974, 30, 2791-2796.
63. Fahmy, S. M.; Abed, N. M.; Mohareb, R. M.; Elnagdi, M. H. Activated nitriles in heterocyclic synthesis: Novel synthesis of pyridazines, pyridines, and isoxazoles. Synthesis, 1982, 490-493.
64. Mohamed, M. H.; Ibrahim, N. S.; Elnagdi, M. H. Nitriles in heterocyclic synthesis: Synthesis of some new pyridine, pyridazine, and pyrimidine derivatives. Heterocycles, 1987, 26, 899-902.
65. Sadek, K. U.; Selim, M. A.; Elmaghraby, M. A.; Elnagdi, M. H. Nitriles in organic synthesis: Synthesis of polyfunctionally substituted pyridine and benzene derivatives. Pharmazie, 1993, 48, 419-422.
66. Elmoghayar, M. R. H.; Elagamey, A. G. A.; Nasr, M. Y. S.; Sallam, M. M. M. Activated nitriles in heterocyclic synthesis. Part III. Synthesis of Namino- 2-pyridone, pyranopyrazole and thiazolopyridine derivatives. J. Heterocycl. Chem., 1984, 21, 1885-1887.
67. Abdel-Galil, F. M.; Abdel-Motaleb, R. M.; Elnagdi, M. H. Nitriles in heterocyclic synthesis. The reaction of acetophenonylidenemalononitrile with some active methylene reagents and acrylonitrile derivatives. An. Quim., Ser. C, 1988, 84, 19-21; Chem. Abstr., 1989, 110, 75387e.
68. Mustafa, N.; Elnagdi, M. H.; Abdel-Aziz, E. H.; Ibrahim, E. Activated nitriles in heterocyclic synthesis. The reaction of cinnamonitrile derivative with active methylene reagents. J. Heterocycl. Chem., 1984, 21, 1261-1264.
69. Abdel-Latif, F. F. Synthesis of several new pyridinone derivatives. Rev. Roum. Chim., 1990, 35, 679-682; Chem. Abstr., 1991, 114, 228683h.
70. Zayed, E. M.; Hafez, E. A.; Ghozlan, S. A. S.; Ibrahim, A. A. H. Activated nitriles in heterocyclic synthesis: The reaction of cyanoacetohydrazide with α-substituted cinnamonitrile derivatives. Heterocycles, 1984, 22, 2553-2558.
71. Basyouni, W. M. Synthesis of novel substituted [1,2,4]triazolo[1,5- a]pyridines and their related pyrano[2,3-d]imidazole derivatives. Acta Chem. Slov., 2003, 50, 223-238.
72. Elgemeie, G. H; Sayed, S. H. Regioselective synthesis of a new class of Narylsulfonylaminated biheterocycles. Phosphorus Sulfur Silicon Rel. Elem., 2003, 178, 465-473.
73. Sadek, K. U.; Mourad, A. E.; Abdelhafeez, A. E.; Elnagdi, M. H. Activated nitriles in heterocyclic synthesis: Synthesis and reactivity of 4-oxo-4,5- dihydro-1,3-thiazol-2-acetamide. Synthesis, 1983, 739-741.
74. Ibrahim, N. S.; Abed, N. M.; Kandeel, Z. E. Nitriles in heterocyclic synthesis: A new approach for the synthesis of thiazinones. Heterocycles, 1984, 22, 1677-1682.
75. Uchikawa, O.; Fukatsu, K.; Tokunoh, R.; Kawada, M.; Matsumoto, K.; Imai, Y.; Hinuma, S.; Kato, K.; Nishikawa, H.; Hirai, K.; Miyamoto, M.; Ohkawa, S. Synthesis of a novel series of tricyclic indan derivatives as melatonin receptor agonists. J. Med. Chem., 2002, 45, 4222-4239.
76. Bench, B. J.; Suarez, V. H.; Watanabe, C. M. H. An efficient one-pot synthesis of tethered cyclohexadiene enaminonitriles from methyl-ketones: An effective route to quinazolines. Bioorg. Med. Chem. Lett., 2007, 18, 3126-3130.
77. Hassan, A. A.; El-Shaieb, K. M.; Shaker, R. M.; Döpp, D. New access to pyrazole, oxa(thia)diazole and oxadiazine derivatives. Heteroatom Chem., 2005, 16, 12-19.
78. Gohar, A. M. N.; Abdel-Latif, F. F.; El-Ktatny, M. S. Synthesis and biological activity of some 5-substituted 1,2,5a,6,11b,11c-hexahydro[1]benzopyrano[ 4,3-d]pyrazolo[3,4-b]pyridine-1,6-diones and 5H-4a,10b-dihydrobenzopyrano[ 3,4-c]pyridine derivatives. Indian J. Chem., 1986, 25B, 404-406.
79. Metwally, N. H.; Abdelrazek, F. M. Reaction of anthranilonitrile with some active methylene reagents: Synthesis of some new quinoline and quinazoline derivatives. Synth. Commun., 2005, 35, 2481-2487.
80. El-Taweel, F. M.; Elmougi, S. M.; Elagamey, A. The condensation of active methylene reagents with salicylaldehyde: Novel synthesis of chromene, azaanthracene, pyrano[3,4-c]chromene and chromeno[3,4-c]pyridine derivatives. J. Heterocycl. Chem., 2004, 41, 655-658.
81. Elnagdi, M. H.; Elmoghayar, M. R. H.; Elgemeie, G. E. H. The chemistry of 3-oxoalkanenitriles. Synthesis 1984, 1-26.
82. Stanovnik, B.; Svete, J. Synthesis of heterocycles from alkyl 3-(dimethylamino) propenoates and related enaminones. Chem. Rev., 2004, 104, 2433-2480.
83. El-Rady, E. A.; Khalil, M. A. 2-cyanoacetamide in the synthesis of heterocyclic compounds: synthesis of new polysubstituted pyrazole, pyridine and pyrimidine derivatives. J. Chin. Chem. Soc., 2004, 51, 779-784.
84. Krivokolysko, S. G.; Litvinov, V. P. Isolation of a stable Michael adduct - An intermediate in the synthesis of sulfur-containing aminopyridines [2]. Chem. Heterocycl. Compd., 2000, 36, 478-479.
85. Ershov, L. V.; Granik, V. G. Acetals of lactams and amides. 45. Synthesis of condensed 2-pyridones based on activated amides, lactams and lactones. Kim. Geterotsikl. Soedin 1985, 7, 929-932; Chem. Abstr., 1986, 104, 168389.
86. Oukli, N.; Comesse, S.; Chafi, N.; Oulyadi, H.; Daich, A. Unexpected reversible nitrogen atom transfer in the synthesis of polysubstituted imides and 7-aza-hexahydroindolones via enaminonitrile γ -lactams. Tetrahedron Lett., 2009, 50, 1459-1462.
87. 1H) coupling constants. J. Chem. Soc. Chem. Commun., 1991, 419-421.
88. 1H J-resolution spectroscopy. Magn. Reson. Chem., 1993, 31, 90-93.
89. 1H long-range coupling constants in configuration assignment of some trisubstituted alkenes. Magn. Reson. Chem., 1994, 32, 567-568.
90. Golic-Grdadolnik, S.; Stanovnik, B. NMR studies of substituted 2,3- diaminopropenoates. Magn. Reson. Chem., 1997, 35, 482-486.
91. Chatterjee, A.; Mishra, M.; Dutta Chowdhury, S. K.; Mahalanabis, K. K. One-pot conversion of β-aminocrotononitrile to secondary enaminonitriles including chiral ones - Application to synthesis. Can. J. Chem., 2005, 83, 1164-1170.
92. Stanovnik, B.; Svete, J. Alkyl 2-substituted 3-(dimethylamino)propenoates and related compounds-versatile reagents in heterocyclic chemistry. Synlett, 2000, 1077-1091.
93. Skof M.; Svete, J.; Stanovnik, B.; Golic-Grdadolnik, S. Synthesis of (2S)-2- (benzoylamino)-3-(heteroaryl)propyl benzoates. Helv. Chim. Acta, 2000, 83, 760-766.
94. Svete, J. Synthesis of heteroaryl substituted α-amino acid derivatives, polyols, and related compounds. J. Heterocycl. Chem., 2002, 39, 437-454.
95. Hussin, A. M.; Abu-Shanab, F. A.; Abd-Elraheim, M. A. M.; Gaby, M. S. A. Synthesis of some novel benzothiazole derivatives. Phosphorus Sulfur Silicon Rel. Elem., 2008, 183, 1722-1734.
96. Ismail, M. M.; Kandeel, M. M. Reactions of 3,5-dichlorosalicylaldehyde with acylglycine derivatives and certain enamines. Rev. Roum. Chim., 1994, 39, 183-188; Chem. Abstr., 1994, 121, 280502g.
97. Almazora, S.; Elnagdi, M. H.; El-Din, A. M. S. Studies with enaminones: The reaction of enaminones with aminoheterocycles. A route to azolopyrimidines, azolopyridines, and quinolines. J. Heterocycl. Chem., 2004, 41, 267-272.
98. El-Enezi, A.; Al-Saleh, B.; Elnagdi, M. H. Studies with heteroaromatic amines: The reaction of some heteroaromatic amines with 1-substituted 3- dimethylaminopropanones, enaminones and cinnamonitriles. J. Chem. Res. (s), 1997, 4-5.
99. Al-Saleh, B.; Al-Awad, N.; Al-Kandari, H.; Abdel Khalik, M. M.; Elnagdi, M. H. Studies with 2H-pyranones: Synthesis of new 3-substituted-4- hydroxy-2H-pyran-2-ones. J. Chem. Res. (S), 2000, 16-17.
100. Skof, M.; Svete, J.; Kmetic, M.; Golic-Grdadolnik, S.; Stanovnik, B. Stereoselective amination of 5-substituted ń-lactones and ń-lactams- A convenient route for the preparation of 5-substituted (3S,5S)-3-acetylaminotetrahydrofuran- 2-ones and (3S,5S)-3-acetylaminopyrrolidin-2-ones. Eur. J. Org. Chem., 1999, 1581-1584.
101. Kmetic, M.; Stanovnik, B. Nitrosation of methyl 2-cinnamoylamino-3- dimethylamino-propenoates. Alkyl N-cinnamoyloxalic acid hydroxyimidic amides, intermediates in the synthesis of alkyl 5-styryl-1,2,4-oxadiazole-3- carboxylates. J. Heterocycl. Chem., 1997, 34, 1705-1708.
102. Jukic, L.; Svete, J.; Golobic, A.; Golic, L.; Stanovnik, B. A synthesis and transformations of alkyl 2-[2-cyano-2-(2-pyridinyl)ethenyl]amino-3- dimethylamino propenoates. A one-pot synthesis of pyrrolo[3,2-d]pyrimidin- 4-ones. Heterocycles, 2000, 53, 805-820.
103. Kostyuk, A. N.; Suyaschenko, Y. V.; Volochnyuk, D. M. New approach to ń5-phosphinines. Tetrahedron, 2005, 61, 9263-9272.
104. Bratusek, U.; Hvala, A.; Stanovnik, B. The synthesis of 3-[(dimethylamino) (2-phenyl-5-oxo-2-oxazolinylidene-4)methyl]imidazo[1,2-x]azines and related compounds, intermediates in the formation of azaaplysinopsin derivatives. J. Heterocycl. Chem., 1998, 35, 971-976.
105. Selic, L.; Stanovnik, B. A new approach to 5H-pyrrolo[3,2-d]pyrimidines (9 deazapurines) from 3-aminopyrrole-2-carboxylates. Heterocycles 1999, 51, 1087-1092.
106. Salaheldin, A. M. Enaminonitriles in heterocyclic synthesis: Novel synthesis of 3-aminopyrroles and pyrrolo[3,2-d]pyrimidine derivatives. Z. Naturforsch., 2008, 63b, 564-570.
107. Selic, L.; Stanovnik, B. Transformations of ethyl 3-{[1-(alkoxycarbonyl)-2- (dimethylamino)ethenyl]amino}-2-cyanoprop-2-enoates: Synthesis of dialkyl 3-aminopyrrole-2,4-dicarboxylates. Helv. Chim. Acta, 1998, 81, 1634-1639.
108. Mukherjee, A.; Mishra, M.; Chatterjee, A.; Sarkar, M.; Chowdhury, S. K. D.; Mahalanabis, K. K. On the regiospecificity of 3,5-disubstituted pyrazoles derived from C-acylated-β-enaminonitriles and esters. Indian J. Chem., 2005, 44B, 2333-2337.
109. Salaheldin, A. M.; Alphy, M. K. Studies with enaminonitriles: Synthesis and chemical reactivity of 2-phenyl-3-piperidin-1-yl acrylonitrile under microwave heating. J. Heterocycl. Chem., 2008, 45, 307-310.
110. Ghozlan, S. A. S.; Abdelhamid, I. A.; Elnagdi, M. H.; Gaber, H. M. Studies with enaminonitriles: A new synthesis of 1,3-substituted pyrazole-4- carbonitrile. J. Heterocycl. Chem., 2005, 42, 1185-1198.
111. Bratusek, U.; Meden, A.; Svete, J.; Stanovnik, B. Transformations of (Z)-2- benzoylamino-4-dimethylamino-2-oxo-3-butene and (E)-3-benzoylamino-4- cyano-2-oxo-3-butene into pyrimidine, pyrazole andisoxazole derivatives. Arkivoc 2003, v, 77-86.
112. Radwan, M. A. A.; Ragab, E. A.; Shaaban, M. R.; El-Nezhawy, A. O. H. Application of (2Z)-3-dimethylamino-2-(1H-indole-3-carbonyl)acrylonitrile in the synthesis of novel 3-heteroarylindoles: Condensed meridianine analogs. Arkivoc 2009, vii, 281-291.
113. Shamroukh, A. H.; Rashad, A. E.; Sayed, H. H. Synthesis of some pyrazolo[ 3,4-d]pyrimidine derivatives for biological evaluation. Phosphorus Sulfur Silicon Rel. Elem., 2005, 180, 2347-2360.
114. Kraus, H. Process for preparation of 2,5-disubstituted pyridines. Ger. Offen. DE 4,223,013 (CI. 07D213/61), 1994; Chem. Abstr., 1994, 120, 191552k.
115. Pilipecz, M. V.;Varga, T. R.; Mucsi, Z.; Scheiber, P.; Nemes, P. [3+3] Cyclization reactions of β-enaminonitriles with α,β -unsaturated carboxylic acid chlorides. Tetrahedron 2008, 64, 5545-5550.
116. Al-Mousawi, S. M.; Kaul, K.; Mohamed, M. A.; Elnagdi, M. H. Studies with condensed azines: New routes to pyrazolo[3,4-b]pyridines and pyrrolo[3,2- b]pyridines. J. Chem. Res. (S), 1997, 318-319.
117. Al-Zaydi, K. M.; Al-Shiekh, M. A. A.; Hafez. Enaminonitriles in heterocyclic synthesis: New routes for the synthesis of some novel azolo[1,5- a]pyrimidine, pyrimido[1,2-a]benzimidazole, pyrido[1,2-a]benimdazole, pyrazolo[3,4-b]pyridine, pyrazole and pyrimidine derivatives. E. A. J. Chem. Res. (S), 2000, 13-15.
118. Al-Saleh, B.; El-Apasery, M. A.; Abdel-Aziz, R. S.; Elnagdi, M. H. Enaminones in heterocyclic synthesis: Synthesis and chemical reactivity of 3- anilino-1-substituted-2-propene-1-one. J. Heterocycl. Chem., 2005, 42, 563-566.
119. Mohamed, N. R.; El-Saidi, M. M. T.; Ali, Y. M.; Elnagdi, M. H. Utility of 6- amino-2-thiouracil as a precursor for the synthesis of bioactive pyrimidine derivatives. Bioorg. Med. Chem. Lett., 2007, 15, 6227-6235.
120. Mohamed, N. R.; El-Saidi, M. M. T.; Ali, Y. M.; Elnagdi, M. H. Utility of 6- amino-2-thiouracil as a precursor for the synthesis of pyrido[2,3- d]pyrimidines and their in vitro and in vivo biological evaluation. Sci. Farm., 2007, 75, 9-28.
121. Elnagdi, M. H.; Elmoghayer, M. R. H.; Fleita, D. H.; Hafez, E. A. A.; Fahmy, S. M. Pyrimidine derivatives and related compounds. 4. A route for the synthesis of pyrazolo[3,4-e]-as-triazines, pyrazolo[3,4-d]pyrimidines, and pyrazolo[1,5-c]-as-triazines. J. Org. Chem., 1976, 41, 3781-3784.
122. Maruoka, H.; Okabe, F.; Yamagata, K. An efficient synthesis of 4-alkoxy- 5,6-dihydro-furo(and-thieno)[2,3-d]pyrimidines using Zinc chloride / triethylamine reagent. J. Heterocycl. Chem., 2008, 45, 541-545.
123. Pizzioli, L.; Ornik, B.; Svete, J.; Stanovnik, B. Synthesis and transformations of methyl (E)-2-(acetylamino)-3-cyanoprop-2-enoate and methyl (E)-2- (benzoylamino)-3-cyanoprop-2-enoate, versatile reagents for the preparation of polyfunctional heterocyclic systems. Helv. Chim. Acta, 1998, 81, 231-235.
124. Elnagdi, M. H.; Negm, A. M.; Erian, A. W. Studies with alkylheteroaromatic π -deficient compounds: Novel synthesis of thieno[3,4-d]pyridazines and phthalazines. Liebigs Ann. Chem., 1989, 1255-1256.
125. Bondock, S.; Fadaly, W.; Metwally, M. A. Enaminonitrile in heterocyclic synthesis: Synthesis and antimicrobial evaluation of some new pyrazole, isoxazole and pyrimidine derivatives incorporating a benzothiazole moiety. Eur. J. Med. Chem., 2009, 44, 4813-4818.
126. Al-Saleh, B.; Abdelkhalik, M. M.; Eltoukhy, A. M.; Elnagdi, M. H. Enaminones in heterocyclic synthesis: A new regioselective synthesis of 2,3,6- trisubstituted pyridines, 6-substituted-3-aroylpyridines and 1,3,5- triaroylbenzenes. J. Heterocycl. Chem., 2002, 39, 1035-1038.
127. Al-Saleh, B.; Abdel Khalik, M. M.; Al-Enezi, A.; Elnagdi, M. H. Synthesis of new azoloazine derivatives: New routes to 1,2,4-triazolo[4,3- a]pyrimidines, pyrazolo[1,5-a]pyridines and pyrazolo[3,4-b]pyridinones. J. Chem. Res. (S), 1999, 654-655.
128. Hafiz, I. S. A.; Ramiz, M. M. M.; Mahmoud, F. F.; Darwish, E. S. β- Enaminonitriles in heterocyclic synthesis: Synthesis of new tetrahydropyridinethione, pyridopyrimidines, pyridotriazines and dihydropyridines. J. Chem. Sci., 2008, 120, 339-345.
129. Calvo, L. A.; Gonzalez-Ortega, A; Marcos, R.; Perez, M.; Sanudo, M. C. Synthesis of 2,3,4,7-tetrahydro[1,4]thiazepines from thiazolidines and β- enaminonitriles. Tetrahedron, 2008, 64, 3691-3700.
130. Mahalanabis, K. K.; Sarkar, M.; Chowdhury, S. K. D.; Ghosal, C. R. Studies on β-enaminonitriles: Part IV- Reaction of β-enaminonitriles with acid chlorides. Indian J. Chem., 2002, 41B, 1902-1906.
131. Al-Awadi, N. A.; Abdel Khalik, M. M. Abdelhamid, I. A.; Elnagdi, M. H. Pyrolytic methods in organic synthesis: Novel routes for the synthesis of 3- oxoalkanenitriles, 2-acyl anilines, and 2-aroyl anilines. Synlett, 2007, 2979-2982.
132. Ashorn, P.; McQuade, T. J.; Thaisrivongs, S.; Tomasselli, A. G.; Tarpley, W. G.; Moss, B. An inhibitor of the protease blocks maturation of human and simian immunodeficiency viruses and spread of infection. Proc. Natl. Acad. Sci. USA, 1990, 87, 7472-7476.
133. Romines, K. R.; Watenpaugh, K. D.; Tomich, P. K.; Howe, W. J.; Morris, J. K.; Lovasz, K. D.; Mulichak, A. M.; Finzel, B. C.; Lynn, J. C.; Horng, M. M.; Schwende, F. J.; Ruwart, M. J.; Zipp, G. L.; Chong, K. T.; Dolak, L. A.; Toth, L. N.; Howard, G. M.; Rush, B. D.; Wilkinson, K. F.; Possert, P. L.; Dalga, R. J.; Hinshaw, R. R. Use of medium-sized cycloalkyl rings to enhance secondary binding: Discovery of a new class of human immunodeficiency virus (HIV) protease inhibitors. J. Med. Chem., 1995, 38, 1884-1891.
134. Wang, S.; Milne, G. W. A.; Yan, X.; Posey, I. J.; Nicklaus, M. C.; Graham, L.; Rice, W. G. Discovery of novel, non-peptide HIV-1 protease inhibitors by pharmacophore searching. J. Med. Chem., 1996, 39, 2047-2054.
135. Strah, S.; Grdadolnik, S. G.; Stanovnik, B. Alkyl 2-(2-benzoyl-2- ethoxycarbonyl-1-ethenyl)amino-3-dimethylaminopropenoates in the synthesis of heterocyclic systems. J. Heterocycl. Chem., 1997, 34, 263-267.
136. Perrier, V.; Wallace, A. C.; Kaneko, K.; Safar, J.; Prusiner, S. B.; Cohen, F. E. Mimicking dominant negative inhibition of prion replication through structure-based drug design. Proc. Natl. Acad. Sci. U.S.A., 2000, 97, 6037-6078.
137. Pan, K. M.; Baldwin, M.; Nguyen, J.; Gasset, M.; Serban, A.; Groth, D.; Mehlhorn, I.; Huang, Z. W.; Fletterick, R. J.; Cohen, F. E.; Prusiner, S. B. Conversion of α -helices into β-sheets features in the formation of the scrapie prion proteins. Proc. Natl. Acad. Sci. U.S.A., 1993, 90, 10962-10966.
138. Hoepping, A.; Diekers, M.; Deuther-conrad, W.; Scheunemann, M.; Fischer, S.; Hiller, A.; Wegner, F.; Steinbach, J.; Brust, P. Synthesis of fluorine substituted pyrazolopyrimidines as potential leads for the development of PETimaging agents for the GABAA receptors. Bioorg. Med. Chem., 2008, 16, 1184-1194.
139. Jiang, B.; Yang, C. G.; Xiong, W. N.; Wang, J. Synthesis and cytotoxicity evaluation of novel indolylpyrimidines and indolylpyrazines as potential antitumor agents. Bioorg. Med. Chem., 2001, 9, 1149-1154.
140. Franco, L. H.; Joffe, E. B. K.; Puricelly, L.; Tatian, M.; Seldes, A. M.; Palermo, J. A. Indole alkaloids from the tunicate Aplidium meridianum. J. Nat. Prod., 1998, 61, 1130-1132.
141. Thompson, C.; Moore, J. A. Synthesis and characterization of aromaticaliphatic poly(enaminonitriles). Polymer, 2000, 41, 4991-5000.
142. Han, D. W.; Moore, J. A. Synthesis and characterization of adamantanecontaining poly(enaminonitriles). Polymer, 2009, 50, 2551-2557.
143. Dworczak, R.; Fabian, W. M. F.; Kieslinger, D.; Junek, H. Azomethines with nonlinear optical properties and polyesters covalently functionalized with them. Syntheses with nitrites. Dyes and Pigments, 1997, 34, 13-23.
144. Vanmaele, L. J. New dyes derived from malononitrile dimmer. Tetrahedron Lett., 1992, 33, 961-964.
145. Cavanagh, D.; James, M. R.; Meyrick, B. H. Pyrrolinone or -thione dyes with dicyanomethylene substituents, their mixtures, and their use in dyeing textiles. PCT Int. Appl. WO 9410,248, 1994; Chem. Abstr., 1994, 121, 181933s.
146. Shimada, Y. Dyes for inks. Jpn. Kokai Tokai Tokkyo JP 04,202,261, 1993; Chem. Abstr., 1993, 118, 40822f.