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Volumn 15, Issue 1, 2013, Pages 2-9

Efficient catalyst-free four-component synthesis of novel γ-aminoethers mediated by a mannich type reaction

Author keywords

aminoethers; alkylbenzylamines; etherification reaction; Mannich type reaction; multicomponent reactions

Indexed keywords

BENZYLAMINE DERIVATIVE; ETHER DERIVATIVE;

EID: 84872544899     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co300105t     Document Type: Article
Times cited : (31)

References (28)
  • 1
    • 84872524109 scopus 로고    scopus 로고
    • Multicomponent Reactions- Superior Chemistry Technology for the New Millennium
    • April 5
    • Dömling, A. Multicomponent Reactions- Superior Chemistry Technology For The New Millennium. Org. Chem. Highlights 2005, April 5.
    • (2005) Org. Chem. Highlights
    • Dömling, A.1
  • 2
    • 78349257436 scopus 로고    scopus 로고
    • Multicomponent Reactions for the Synthesis of He terocycles
    • Jiang, B.; Rajale, T.; Wever, W.; Tu, S-J; Li, G. Multicomponent Reactions for the Synthesis of He terocycles Chem. Asian J. 2010, 5 (11) 2318-2335
    • (2010) Chem. Asian J. , vol.5 , Issue.11 , pp. 2318-2335
    • Jiang, B.1    Rajale, T.2    Wever, W.3    Tu, S.-J.4    Li, G.5
  • 3
    • 84055182866 scopus 로고    scopus 로고
    • A Multi-component Domino Reaction for the Direct Access to Polyfunctionalized Indoles via Intermolecular Allylic Esterification and Indolation
    • Jiang, B.; Yi, M.-S.; Shi, F.; Tu, S.-J.; Pindi, S.; McDowell, P.; Li, G. A Multi-component Domino Reaction for the Direct Access to Polyfunctionalized Indoles via Intermolecular Allylic Esterification and Indolation Chem. Commun. 2012, 48, 808-810
    • (2012) Chem. Commun. , vol.48 , pp. 808-810
    • Jiang, B.1    Yi, M.-S.2    Shi, F.3    Tu, S.-J.4    Pindi, S.5    McDowell, P.6    Li, G.7
  • 4
    • 84862175237 scopus 로고    scopus 로고
    • Chemistry and Biology of Multicomponent Reactions
    • Dömling, A.; Wang, W.; Wang, K. Chemistry and Biology of Multicomponent Reactions Chem. Rev. 2012, 112 (6) 3083-3135
    • (2012) Chem. Rev. , vol.112 , Issue.6 , pp. 3083-3135
    • Dömling, A.1    Wang, W.2    Wang, K.3
  • 5
    • 0037028990 scopus 로고    scopus 로고
    • A Highly Enantioselective Route to Either Enantiomer of Both α- And β-Amino Acid Derivatives
    • Cordoba, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F. A Highly Enantioselective Route to Either Enantiomer of Both α- and β-Amino Acid Derivatives J. Am. Chem. Soc. 2002, 124 (9) 1866-1867
    • (2002) J. Am. Chem. Soc. , vol.124 , Issue.9 , pp. 1866-1867
    • Cordoba, A.1    Watanabe, S.2    Tanaka, F.3    Notz, W.4    Barbas, C.F.5
  • 6
    • 64249099123 scopus 로고    scopus 로고
    • Efficient Three-Component Strecker Reaction of Aldehydes/Ketones via NHC-Amidate Palladium(II) Complex Catalysis
    • Jarusiewicz, J.; Choe, Y.; Yoo, K. S.; Park, C. P.; Jung, K. W. Efficient Three-Component Strecker Reaction of Aldehydes/Ketones via NHC-Amidate Palladium(II) Complex Catalysis J. Org. Chem. 2009, 74, 2873-2876
    • (2009) J. Org. Chem. , vol.74 , pp. 2873-2876
    • Jarusiewicz, J.1    Choe, Y.2    Yoo, K.S.3    Park, C.P.4    Jung, K.W.5
  • 7
    • 42049089739 scopus 로고    scopus 로고
    • Efficient Synthesis of Hantzsch Esters and Polyhydroquinoline Derivatives in Aqueous Micelles
    • Kumar, A.; Maurya, R. A. Efficient Synthesis of Hantzsch Esters and Polyhydroquinoline Derivatives in Aqueous Micelles Synlett 2008, 883-885
    • (2008) Synlett , pp. 883-885
    • Kumar, A.1    Maurya, R.A.2
  • 8
    • 5644259644 scopus 로고    scopus 로고
    • A Versatile Synthesis of Fused Triazolo Derivatives by Sequential Ugi/Alkyne-Azide Cycloaddition Reactions
    • Akritopoulou-Zanze, I.; Gracias, V.; Djuric, S. W. A Versatile Synthesis of Fused Triazolo Derivatives by Sequential Ugi/Alkyne-Azide Cycloaddition Reactions Tetrahedron Lett. 2004, 45, 8439-8441
    • (2004) Tetrahedron Lett. , vol.45 , pp. 8439-8441
    • Akritopoulou-Zanze, I.1    Gracias, V.2    Djuric, S.W.3
  • 9
    • 33947544770 scopus 로고    scopus 로고
    • N -Substituted Ureas and Thioureas in Biginelli Reaction Promoted by Chlorotrimethylsilane: Convenient Synthesis of N 1-Alkyl-, N 1-Aryl-, and N 1, N 3-Dialkyl-3,4-Dihydropyrimidin-2(1 H)-(thi)ones
    • Ryabukhin, S. V.; Plaskon, A. S.; Ostapchuk, E. N.; Volochnyuk, D. M.; Tolmachev, A. A. N -Substituted Ureas and Thioureas in Biginelli Reaction Promoted by Chlorotrimethylsilane: Convenient Synthesis of N 1-Alkyl-, N 1-Aryl-, and N 1, N 3-Dialkyl-3,4-Dihydropyrimidin-2(1 H)-(thi)ones Synthesis 2007, 417-427
    • (2007) Synthesis , pp. 417-427
    • Ryabukhin, S.V.1    Plaskon, A.S.2    Ostapchuk, E.N.3    Volochnyuk, D.M.4    Tolmachev, A.A.5
  • 10
    • 33745712075 scopus 로고    scopus 로고
    • Revisiting the Passerini Reaction under Eco-Friendly Reaction Conditions
    • 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, 1539-1541
    • (2006) Synlett , pp. 1539-1541
    • Andrade, C.K.Z.1    Takada, S.C.S.2    Suarez, P.A.Z.3    Alves, M.B.4
  • 11
    • 35648979560 scopus 로고    scopus 로고
    • Efficient Synthesis of Thiobenzanilides by Willgerodt-Kindler Reaction with Base Catalysts
    • Okamoto, K.; Yamamoto, T.; Kanbara, T. Efficient Synthesis of Thiobenzanilides by Willgerodt-Kindler Reaction with Base Catalysts Synlett. 2007, 2687-2690
    • (2007) Synlett. , pp. 2687-2690
    • Okamoto, K.1    Yamamoto, T.2    Kanbara, T.3
  • 12
    • 7044235263 scopus 로고    scopus 로고
    • Domino Reactions in Organic Synthesis
    • Tietze, L. F. Domino Reactions in Organic Synthesis Chem. Rev. 1996, 96, 115-136
    • (1996) Chem. Rev. , vol.96 , pp. 115-136
    • Tietze, L.F.1
  • 15
    • 66249111475 scopus 로고    scopus 로고
    • Spiroborate Ester-Mediated Asymmetric Synthesis of β-Hydroxy Ethers and Its Conversion to Highly Enantiopure β-Amino Ethers
    • Huang, K.; Ortiz-Marciales, M.; Correa, W.; Pomales, E.; López, X. Y. Spiroborate Ester-Mediated Asymmetric Synthesis of β-Hydroxy Ethers and Its Conversion to Highly Enantiopure β-Amino Ethers J. Org. Chem. 2009, 74, 4195-4202
    • (2009) J. Org. Chem. , vol.74 , pp. 4195-4202
    • Huang, K.1    Ortiz-Marciales, M.2    Correa, W.3    Pomales, E.4    López, X.Y.5
  • 16
    • 0027399143 scopus 로고
    • Third-Generation Antidepressants
    • Pinder, R. M.; Wieringa, J. H. Third-Generation Antidepressants Med. Res. Rev. 1993, 13, 259-325
    • (1993) Med. Res. Rev. , vol.13 , pp. 259-325
    • Pinder, R.M.1    Wieringa, J.H.2
  • 17
    • 78649286495 scopus 로고    scopus 로고
    • An Efficient Synthesis of 7-(Arylmethyl)-3- tert -butyl-1-phenyl-6,7- dihydro-1 H,4 H -pyrazolo[3,4- d ][1,3]oxazines
    • Abonia, R.; Castillo, J.; Insuasty, B.; Quiroga, J.; Nogueras, M.; Cobo, J. An Efficient Synthesis of 7-(Arylmethyl)-3- tert -butyl-1-phenyl-6,7-dihydro- 1 H,4 H -pyrazolo[3,4- d ][1,3]oxazines Eur. J. Org. Chem. 2010, 6454-6463
    • (2010) Eur. J. Org. Chem. , pp. 6454-6463
    • Abonia, R.1    Castillo, J.2    Insuasty, B.3    Quiroga, J.4    Nogueras, M.5    Cobo, J.6
  • 18
    • 67650770195 scopus 로고    scopus 로고
    • Seven 5-Benzylamino-3- tert -butyl-1-phenyl-1 H -pyrazoles: Unexpected Isomorphisms, and Hydrogen-Bonded Supramolecular Structures in Zero, One and Two Dimensions
    • Castillo, J.; Abonia, R.; Cobo, J.; Glidewell, C. Seven 5-Benzylamino-3- tert -butyl-1-phenyl-1 H -pyrazoles: Unexpected Isomorphisms, and Hydrogen-Bonded Supramolecular Structures in Zero, One and Two Dimensions Acta Crystallogr. 2009, C65, o303-o310
    • (2009) Acta Crystallogr. , vol.65
    • Castillo, J.1    Abonia, R.2    Cobo, J.3    Glidewell, C.4
  • 19
    • 0034121281 scopus 로고    scopus 로고
    • Cell Cycle Molecular Targets in Novel Anticancer Drug Discovery
    • Buolamwini, J. K. Cell Cycle Molecular Targets in Novel Anticancer Drug Discovery Curr. Pharm. Des. 2000, 6, 379-392
    • (2000) Curr. Pharm. Des. , vol.6 , pp. 379-392
    • Buolamwini, J.K.1
  • 20
    • 0016773917 scopus 로고
    • Studies on the Synthesis of Analgesics. IV. Synthesis of 1,2,3,4-Tetrahydro-5 H -benzazepine Derivatives
    • Sawa, Y.; Kato, T.; Masuda, T.; Hori, M.; Fujimura, H. Studies on the Synthesis of Analgesics. IV. Synthesis of 1,2,3,4-Tetrahydro-5 H -benzazepine Derivatives Chem. Pharm. Bull. 1975, 23 (9) 1917-1927
    • (1975) Chem. Pharm. Bull. , vol.23 , Issue.9 , pp. 1917-1927
    • Sawa, Y.1    Kato, T.2    Masuda, T.3    Hori, M.4    Fujimura, H.5
  • 22
    • 0020595626 scopus 로고
    • SCH 23390 - The First Selective Dopamine D-1 Antagonist
    • Hyttel, J. SCH 23390-The First Selective Dopamine D-1 Antagonist Eur. J. Pharmacol. 1983, 91 (1) 153-154
    • (1983) Eur. J. Pharmacol. , vol.91 , Issue.1 , pp. 153-154
    • Hyttel, J.1
  • 23
    • 33747212844 scopus 로고    scopus 로고
    • Direct-Type Catalytic Three-Component Mannich Reactions Leading to an Efficient Synthesis of α,β-Diamino Acid Derivatives
    • Salter, M. M.; Kobayashi, J.; Shimizu, Y.; Kobayashi, S. Direct-Type Catalytic Three-Component Mannich Reactions Leading to an Efficient Synthesis of α,β-Diamino Acid Derivatives Org. Lett. 2006, 8, 3533-3536
    • (2006) Org. Lett. , vol.8 , pp. 3533-3536
    • Salter, M.M.1    Kobayashi, J.2    Shimizu, Y.3    Kobayashi, S.4
  • 24
    • 44349190183 scopus 로고    scopus 로고
    • Diarylborinic Acid Derivatives as a Catalytic Iminium Ion Generator in the Mannich-Type Reaction Using Secondary Amines, Aldehydes, and Ketene Silyl Acetals
    • Tanaka, Y.; Hasui, T.; Suginome, M. Diarylborinic Acid Derivatives as a Catalytic Iminium Ion Generator in the Mannich-Type Reaction Using Secondary Amines, Aldehydes, and Ketene Silyl Acetals Synlett. 2008, 1239-1241
    • (2008) Synlett. , pp. 1239-1241
    • Tanaka, Y.1    Hasui, T.2    Suginome, M.3
  • 25
    • 0031757216 scopus 로고    scopus 로고
    • Synthesis of 3,4,7,8-Tetrahydro-6 H -pyrido[1,2,3- ef ]-1,5-benzodiazepin-2(1 H)-ones via Benzotriazole Methodology
    • Katritzky, A. R.; Abonia, R.; Yang, B.; Qi, M.; Insuasty, B. Synthesis of 3,4,7,8-Tetrahydro-6 H -pyrido[1,2,3- ef ]-1,5-benzodiazepin-2(1 H)-ones via Benzotriazole Methodology Synthesis 1998, 1487-1490
    • (1998) Synthesis , pp. 1487-1490
    • Katritzky, A.R.1    Abonia, R.2    Yang, B.3    Qi, M.4    Insuasty, B.5
  • 26
    • 80053299753 scopus 로고    scopus 로고
    • Intramolecular Povarov Reactions Involving 3-Aminocoumarins
    • Kudale, A.; Miller, D.; Dawe, L.; Bodwell, G. Intramolecular Povarov Reactions Involving 3-Aminocoumarins Org. Biomol. Chem. 2011, 9, 7196-7206
    • (2011) Org. Biomol. Chem. , vol.9 , pp. 7196-7206
    • Kudale, A.1    Miller, D.2    Dawe, L.3    Bodwell, G.4
  • 27
    • 61349084177 scopus 로고    scopus 로고
    • Recent Synthetic Developments in a Powerful Imino Diels-Alder Reaction (Povarov Reaction): Application to the Synthesis of N -Polyheterocycles and Related Alkaloids
    • Kouznetsov, V. Recent Synthetic Developments in a Powerful Imino Diels-Alder Reaction (Povarov Reaction): Application to the Synthesis of N -Polyheterocycles and Related Alkaloids Tetrahedron 2009, 65, 2721-2750
    • (2009) Tetrahedron , vol.65 , pp. 2721-2750
    • Kouznetsov, V.1
  • 28
    • 0000031049 scopus 로고
    • Novel, Metal-Catalyzed Carbonylation of Acyclic Organic Compounds. The Regiospecific Carbonylation of N,S -Acetals
    • 1H NMR spectrum of compound 11 matches with that of compound 1f previously reported in Khumtaveeporn, K.; Alper, H. Novel, Metal-Catalyzed Carbonylation of Acyclic Organic Compounds. The Regiospecific Carbonylation of N,S -Acetals J. Org. Chem. 1994, 59, 1414-1417 and it was obtained from the same precursors although in a different reaction condition
    • (1994) J. Org. Chem. , vol.59 , pp. 1414-1417
    • Khumtaveeporn, K.1    Alper, H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.