메뉴 건너뛰기




Volumn 41, Issue 15, 2011, Pages 2186-2194

Efficient InCl3/H2O-catalyzed one-potstereoselective synthesis of cis-2-methyl-4-amido-1,2,3,4-tetrahydroquinoline derivatives

Author keywords

2 methyl 4 amido 1,2,3,4 tetrahydroquinolines; Imino Diels Alder; Indium trichloride; N vinyllactams; One pot

Indexed keywords

AROMATIC AMINE; CAPROLACTAM; CIS 1 (2 METHYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL)AZEPAN 2 ONE; CIS 1 (2,6 DIMETHYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL)AZEPAN 2 ONE; CIS 1 (2,8 DIMETHYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL)AZEPAN 2 ONE; CIS 1 (6 BROMO 2 METHYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL)AZEPAN 2 ONE; CIS 1 (6 CHLORO 2 METHYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL)AZEPAN 2 ONE; CIS 1 (6 FLUORO 2 METHYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL)AZEPAN 2 ONE; CIS 1 (6 METHOXY 2 METHYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL)AZEPAN 2 ONE; CIS 1 (8 CHLORO 2 METHYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL)AZEPAN 2 ONE; CIS 1 (8 FLUORO 2 METHYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL)AZEPAN 2 ONE; INDIUM CHLORIDE; PYRROLIDINE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 79957642578     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911003650453     Document Type: Article
Times cited : (20)

References (30)
  • 1
    • 30444451289 scopus 로고    scopus 로고
    • Discovery of CP-529,414: A potent synthetic inhibitor of human plasma cholesteryl ester transfer protein (CETP)
    • American Chemical Society: Washington, DC; MEDI-156
    • Ruggeri, R. B.; Wester, R. T.; Magnus-Aryitey, G. Discovery of CP-529,414: A potent synthetic inhibitor of human plasma cholesteryl ester transfer protein (CETP). In Abstracts of Papers, 225th National Meeting of the American Chemical Society, American Chemical Society: Washington, DC; 2003; MEDI-156.
    • (2003) Abstracts of Papers, 225th National Meeting of the American Chemical Society
    • Ruggeri, R.B.1    Wester, R.T.2    Magnus-Aryitey, G.3
  • 6
    • 0030602266 scopus 로고    scopus 로고
    • Recent progress in the synthesis of 1,2,3,4,- tetrahydroquinolines
    • Katritzky, A. R.; Rachwal, S.; Rachwal, B. Recent progress in the synthesis of 1,2,3,4,- tetrahydroquinolines. Tetrahedron 1996, 52, 15031-1507010
    • (1996) Tetrahedron , vol.52 , pp. 15031-1507010
    • Katritzky, A.R.1    Rachwal, S.2    Rachwal, B.3
  • 7
    • 0000354729 scopus 로고
    • αβ-Unsaturated ethers and their analogues in reactions of diene synthesis
    • Povarov, L. S. αβ-Unsaturated ethers and their analogues in reactions of diene synthesis. Russ. Chem. Rev. Engl. Trans. L 1967, 36, 656-670
    • (1967) Russ. Chem. Rev. Engl. Trans. L , vol.36 , pp. 656-670
    • Povarov, L.S.1
  • 9
    • 0343081039 scopus 로고    scopus 로고
    • 3-N-aryl-aldimine
    • DOI 10.1021/jo9918807
    • Crousse, B.; Begue, J.; Bonnet-Delpon, D. Synthesis of 2-CF(3)-tetrahydroquinoline and quinoline derivatives from CF(3)-N-aryl- aldimine. J. Org. Chem. 2000, 65, 5009- 5013 (Pubitemid 30640708)
    • (2000) Journal of Organic Chemistry , vol.65 , Issue.16 , pp. 5009-5013
    • Crousse, B.1    Begue, J.-P.2    Bonnet-Delpon, D.3
  • 11
    • 0000621458 scopus 로고    scopus 로고
    • Chem. Abstr. 1998, 129, 95393
    • (1998) Chem. Abstr. , vol.129 , pp. 95393
  • 12
    • 0029123197 scopus 로고
    • Ytterbium(III) triflate-catalyzed synthesis of quinoline derivatives from N-arylaldimines and vinyl ethers
    • Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Ytterbium(III) triflate-catalyzed synthesis of quinoline derivatives from N-arylaldimines and vinyl ethers. Synthesis 1995, 801
    • (1995) Synthesis , pp. 801
    • Makioka, Y.1    Shindo, T.2    Taniguchi, Y.3    Takaki, K.4    Fujiwara, Y.5
  • 13
    • 37049081690 scopus 로고
    • Acid-catalysed addition of N-aryl imines to dihydrofuran: Postulated dependence of the reaction mechanism on the relative face of approach of reactants
    • Lucchini, V.; Prato, M.; Scorrano, G.; Stivanello, M.; Valle, G. Acid-catalysed addition of N-aryl imines to dihydrofuran: Postulated dependence of the reaction mechanism on the relative face of approach of reactants. J. Chem. Soc., Perkin. Trans. 2 1992, 259
    • (1992) J. Chem. Soc., Perkin. Trans. , vol.2 , pp. 259
    • Lucchini, V.1    Prato, M.2    Scorrano, G.3    Stivanello, M.4    Valle, G.5
  • 14
    • 0022616998 scopus 로고
    • Synthesis of 4-heterocyclyl-hexahydro-8-methoxyfuro[3,2-c]quinolines by Lewis acid catalyzed [4 + 2]cycloaddition reaction
    • Kametani, T.; Furuyama, H.; Fukuoka, Y.; Takeda, H.; Suzuki, Y.; Honda, T. Synthesis of 4-heterocyclyl-hexahydro-8-methoxyfuro[3,2-c]quinolines by Lewis acid-catalyzed [4+2] cycloaddition reaction. J. Heterocycl. Chem. 1986, 23, 185-187 (Pubitemid 16111579)
    • (1986) Journal of Heterocyclic Chemistry , vol.23 , Issue.1 , pp. 185-187
    • Kametani, T.1    Furuyama, H.2    Fukuoka, Y.3
  • 15
    • 0032516298 scopus 로고    scopus 로고
    • Convenient synthesis of pyrano[3,2-c]quinolines and indeno[2,1-c] quinolines by imino Diels-Alder reactions
    • Babu, G.; Perumal, P. T. Convenient synthesis of pyrano[3,2-c]quinolines and indeno[2,1-c] quinolines by imino Diels-Alder reactions. Tetrahedron Lett. 1998, 39, 3225
    • (1998) Tetrahedron Lett. , vol.39 , pp. 3225
    • Babu, G.1    Perumal, P.T.2
  • 16
    • 0035963686 scopus 로고    scopus 로고
    • First Asymmetric Synthesis of Quinoline Derivatives by Inverse Electron Demand (IED) Diels-Alder Reaction Using Chiral Ti(IV) Complex
    • DOI 10.1021/ol0159221
    • Sundararajan, G.; Prabagaran, N.; Varghese, B. First asymmetric synthesis of quinoline derivatives by inverse electron demand (IED) Diels-Alder reaction using chiral Ti(IV) complex. Org. Lett. 2001, 3, 1973-1976. (Pubitemid 33631692)
    • (2001) Organic Letters , vol.3 , Issue.13 , pp. 1973-1976
    • Sundararajan, G.1    Prabagaran, N.2    Varghese, B.3
  • 17
    • 0033588330 scopus 로고    scopus 로고
    • Lanthanide chloride-catalyzed imino Diels-Alder reaction: One-pot synthesis of pyrano[3,2-c]- and furo[3,2-c]quinolines
    • Ma, Y.; Qian, C.; Xie, M.; Sun, J. Lanthanide chloride-catalyzed imino Diels-Alder reaction: One-pot synthesis of pyrano[3,2-c]- and furo[3,2-c]quinolines. J. Org. Chem. 1999, 64, 6462-6467
    • (1999) J. Org. Chem. , vol.64 , pp. 6462-6467
    • Ma, Y.1    Qian, C.2    Xie, M.3    Sun, J.4
  • 18
    • 0029813591 scopus 로고    scopus 로고
    • A new methodology for combinatorial synthesis. Preparation of diverse quinoline derivatives using a novel polymer-supported scandium catalyst
    • DOI 10.1021/ja961062l
    • Kobayashi, S.; Nagayama, S. A new methodology for combinatorial synthesis: Preparation of diverse quinoline derivatives using a novel polymersupported scandium catalyst. J. Am. Chem. Soc. 1996, 118, 8977-8978. (Pubitemid 26325172)
    • (1996) Journal of the American Chemical Society , vol.118 , Issue.37 , pp. 8977-8978
    • Kobayashi, S.1    Nagayama, S.2
  • 19
  • 20
    • 0033543497 scopus 로고    scopus 로고
    • Organic syntheses using indium-mediated and catalyzed reactions in aqueous media
    • For reviews on synthetic applications of indium and indium reagents, see
    • For reviews on synthetic applications of indium and indium reagents, see Li, C. J.; Chan, T. H. Organic syntheses using indium-mediated and catalyzed reactions in aqueous media. Tetrahedron 1999, 55, 11149-11176
    • (1999) Tetrahedron , vol.55 , pp. 11149-11176
    • Li, C.J.1    Chan, T.H.2
  • 21
    • 0037571395 scopus 로고
    • Synthetic organoindium chemistry: What makes indium so appealing?
    • Cintas, P. Synthetic organoindium chemistry: What makes indium so appealing? Synlett 1995, 1087
    • (1995) Synlett , pp. 1087
    • Cintas, P.1
  • 23
    • 0033928629 scopus 로고    scopus 로고
    • Indium metal and its halides in organic synthesis
    • Ranu, B. C. Indium metal and its halides in organic synthesis. Eur. J. Org. Chem. 2000, 2347-2356
    • (2000) Eur. J. Org. Chem. , pp. 2347-2356
    • Ranu, B.C.1
  • 25
    • 0037204923 scopus 로고    scopus 로고
    • 3-catalyzed domino reaction of aromatic amines with cyclic enol ethers in water: A highly efficient synthesis of new 1,2,3,4- tetrahydroquinoline derivatives
    • (and references cited therein)
    • 3-catalyzed domino reaction of aromatic amines with cyclic enol ethers in water: A highly efficient synthesis of new 1,2,3,4-tetrahydroquinoline derivatives. J. Org. Chem. 2002, 67, 3969 (and references cited therein).
    • (2002) J. Org. Chem. , vol.67 , pp. 3969
    • Zhang, J.1    Li, C.-J.2
  • 26
    • 40849130002 scopus 로고    scopus 로고
    • Indium chloride-catalyzed intramolecular cyclization of N-arylimines: Synthesis of pyrrolo[2,3-d]pyrimidine annulated tetrahydroquinoline derivatives
    • Ramesh, E.; Raghunathan, R. Indium chloride-catalyzed intramolecular cyclization of N-arylimines: Synthesis of pyrrolo[2,3-d]pyrimidine annulated tetrahydroquinoline derivatives. Tetrahedron Lett. 2008, 49, 2583-2587
    • (2008) Tetrahedron Lett. , vol.49 , pp. 2583-2587
    • Ramesh, E.1    Raghunathan, R.2
  • 27
    • 0037529208 scopus 로고    scopus 로고
    • Dihydropyridine-based multicomponent reactions. Efficient entry into new tetrahydroquinoline systems through Lewis acid-catalyzed formal [4 + 2] cycloadditions
    • DOI 10.1021/ol027545d
    • Lavilla, R.; Carmen Bernabeu, M.; Carranco, I.; Diaz, J. L. Dihydropyridine-based multicomponent reactions: Efficient entry into new tetrahydroquinoline systems through Lewis acid-catalyzed formal [4+2] cycloadditions. Org. Lett. 2003, 5, 717-720. (Pubitemid 37141086)
    • (2003) Organic Letters , vol.5 , Issue.5 , pp. 717-720
    • Lavilla, R.1    Bernabeu, M.C.2    Carranco, I.3    Diaz, J.L.4
  • 28
    • 57449083494 scopus 로고    scopus 로고
    • Synthesis of 1-(2-methyl-1,2,3,4- tetrahydroquinolin-4-yl)pyrrolidin-2- ones from anilines and N-vinyl pyrrolidin-2-one through imino Diels-Alder reaction using 4-nitro phthalic acid as catalyst
    • Srinivasa, A.; Mahadevan, K. M.; Vijaykumar, H. Synthesis of 1-(2-methyl-1,2,3,4- tetrahydroquinolin-4-yl)pyrrolidin-2-ones from anilines and N-vinyl pyrrolidin-2-one through imino Diels-Alder reaction using 4-nitro phthalic acid as catalyst. Synth. Commun. 2009, 39, 93-101.
    • (2009) Synth. Commun. , vol.39 , pp. 93-101
    • Srinivasa, A.1    Mahadevan, K.M.2    Vijaykumar, H.3
  • 29
    • 33748790972 scopus 로고    scopus 로고
    • Cation radical aza-Diels-Alder reaction between N-arylimines and N-vinyllactams: A facile synthesis of 4-lactam-N-yl tetrahydroquinolines
    • DOI 10.1055/s-2006-942521
    • Jia, X.; Han, B.; Zhang, W.; Jin, X.; Yang, L.; Liu, Z.-L. Cation radical aza-Diels-Alder reaction between N-arylimines and N-vinyllactams: A facile synthesis of 4-lactam-n-yl tetrahydroquinolines. Synthesis 2006, 2831-2836. (Pubitemid 44407827)
    • (2006) Synthesis , Issue.17 , pp. 2831-2836
    • Jia, X.1    Han, B.2    Zhang, W.3    Jin, X.4    Yang, L.5    Liu, Z.-L.6
  • 30
    • 33845335853 scopus 로고    scopus 로고
    • CAN-catalyzed three-component reaction between anilines and alkyl vinyl ethers: stereoselective synthesis of 2-methyl-1,2,3,4-tetrahydroquinolines and studies on their aromatization
    • DOI 10.1016/j.tet.2006.11.002, PII S0040402006017649
    • Sridharan, V.; Carmen, A.; Menendez, J. C. CAN-catalyzed three-component reaction between anilines and alkyl vinyl ethers: Stereoselective synthesis of 2-methyl-1,2,3,4- tetrahydroquinolines and studies on their aromatization. Tetrahedron 2007, 63, 673-681. (Pubitemid 44881056)
    • (2007) Tetrahedron , vol.63 , Issue.3 , pp. 673-681
    • Sridharan, V.1    Avendano, C.2    Menendez, J.C.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.