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Volumn 74, Issue 18, 2009, Pages 7052-7058

Construction of nitrogen heterocycles bearing an aminomethyl group by copper-catalyzed domino three-component coupling-cyclization

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC ALDEHYDE; C-H FUNCTIONALIZATION; CHEMICAL EQUATIONS; DIRECT APPROACH; DOMINO REACTIONS; MALONATES; NITROGEN HETEROCYCLES; PARAFORMALDEHYDES; SECONDARY AMINES; THREE-COMPONENT COUPLING;

EID: 70249150445     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901328q     Document Type: Article
Times cited : (104)

References (91)
  • 2
    • 2542509173 scopus 로고    scopus 로고
    • For recent reviews, see: (a)
    • For recent reviews, see: (a) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 3168-3210
    • Dömling, A.1    Ugi, I.2
  • 6
    • 0000721036 scopus 로고    scopus 로고
    • For recent reviews, see: (a)
    • For recent reviews, see: (a) Malacria, M. Chem. Rev. 1996, 96, 289-306.
    • (1996) Chem. Rev. , vol.96 , pp. 289-306
    • Malacria, M.1
  • 10
    • 33746864043 scopus 로고    scopus 로고
    • For recent reviews, see: (a)
    • For recent reviews, see: (a) Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875-2911.
    • (2006) Chem. Rev. , vol.106 , pp. 2875-2911
    • Humphrey, G.R.1    Kuethe, J.T.2
  • 12
    • 85014580919 scopus 로고
    • For recent reviews, see: (a)
    • For recent reviews, see: (a) Bosch, J.; Bennasar, M.-L. Synlett 1995, 587-596.
    • (1995) Synlett , pp. 587-596
    • Bosch, J.1    Bennasar, M.-L.2
  • 18
    • 33746794215 scopus 로고    scopus 로고
    • (g) Lewis, S. E. Tetrahedron 2006, 62, 8655-8681.
    • (2006) Tetrahedron , vol.62 , pp. 8655-8681
    • Lewis, S.E.1
  • 28
    • 33744769419 scopus 로고    scopus 로고
    • For recent synthesis of 2-(aminomethyl)indoles by another approach, see: (a)
    • For recent synthesis of 2-(aminomethyl)indoles by another approach, see: (a) Ambrogio, I.; Cacchi, S.; Fabrizi, G. Org. Lett. 2006, 8, 2083-2086.
    • (2006) Org. Lett. , vol.8 , pp. 2083-2086
    • Ambrogio, I.1    Cacchi, S.2    Fabrizi, G.3
  • 40
    • 26444464330 scopus 로고    scopus 로고
    • For recent reviews, see: (a)
    • For recent reviews, see: (a) Ohno, H. Chem. Pharm. Bull. 2005, 53, 1211-1226.
    • (2005) Chem. Pharm. Bull. , vol.53 , pp. 1211-1226
    • Ohno, H.1
  • 43
    • 70249141932 scopus 로고    scopus 로고
    • For the preparation of 8, see the Supporting Information.
    • For the preparation of 8, see the Supporting Information.
  • 44
    • 13844272578 scopus 로고    scopus 로고
    • For indole synthesis with dihaloarenes, see: (a)
    • For indole synthesis with dihaloarenes, see: (a) Ackermann, L. Org. Lett. 2005, 7, 439-442.
    • (2005) Org. Lett. , vol.7 , pp. 439-442
    • Ackermann, L.1
  • 49
    • 0242712817 scopus 로고    scopus 로고
    • For two-component indole synthesis via a Sonogashira-type reaction, see: (a)
    • For two-component indole synthesis via a Sonogashira-type reaction, see: (a) Cacchi, S.; Fabrizi, G.; Parisi, L. M. Org. Lett. 2003, 5, 3843-3846.
    • (2003) Org. Lett. , vol.5 , pp. 3843-3846
    • Cacchi, S.1    Fabrizi, G.2    Parisi, L.M.3
  • 51
    • 34250351331 scopus 로고    scopus 로고
    • A portion of this study (several reactions in Tables 1, 2, and 5, and Scheme 3) was already reported in a preliminary communication
    • A portion of this study (several reactions in Tables 1, 2, and 5, and Scheme 3) was already reported in a preliminary communication: Ohno, H.; Ohta, Y.; Oishi, S.; Fujii, N. Angew. Chem., Int. Ed. 2007, 46, 2295-2298.
    • (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 2295-2298
    • Ohno, H.1    Ohta, Y.2    Oishi, S.3    Fujii, N.4
  • 52
    • 70249146068 scopus 로고    scopus 로고
    • We consider decreasing the amount of amine component is important and economical especially when using more valuable amines such as 11 (Scheme 4)
    • We consider decreasing the amount of amine component is important and economical especially when using more valuable amines such as 11 (Scheme 4).
  • 53
    • 70249100903 scopus 로고    scopus 로고
    • When benzylamine was used instead of a secondary amine, dimeric compound 18 was produced in 82% yield (100°C, 3 h, then reflux, 1 h). OD-H
    • When benzylamine was used instead of a secondary amine, dimeric compound 18 was produced in 82% yield (100°C, 3 h, then reflux, 1 h). OD-H).
  • 54
    • 70249125334 scopus 로고    scopus 로고
    • When acetone was used instead of an aldehyde, Mannich-type reaction did not proceed and compound 19 was produced
    • When acetone was used instead of an aldehyde, Mannich-type reaction did not proceed and compound 19 was produced.
  • 60
    • 70249084791 scopus 로고    scopus 로고
    • It was reported that the copper-catalyzed Mannich reaction of alkynes in the presence of (R)-QUINAP gave (S)-propargylamines, while the reaction with (S)-PINAP gave the corresponding (R)-isomers, see refs 20 and 21
    • It was reported that the copper-catalyzed Mannich reaction of alkynes in the presence of (R)-QUINAP gave (S)-propargylamines, while the reaction with (S)-PINAP gave the corresponding (R)-isomers, see refs 20 and 21.
  • 61
    • 70249115970 scopus 로고    scopus 로고
    • Knochel and Carreira reported that phenylacetylene is a good component for enantioselective synthesis of propargylic amine with QUINAP or PINAP, see refs 20 and 21
    • Knochel and Carreira reported that phenylacetylene is a good component for enantioselective synthesis of propargylic amine with QUINAP or PINAP, see refs 20 and 21.
  • 62
    • 0027439357 scopus 로고
    • For biologically active polycyclic indoles having a 2-(aminomethyl) moiety, see: (a)
    • For biologically active polycyclic indoles having a 2-(aminomethyl) moiety, see: (a) Espada, A.; Jiménez, C.; Debitus, C.; Riguera, R. Tetrahedron Lett. 1993, 34, 7773-7776.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 7773-7776
    • Espada, A.1    Jiménez, C.2    Debitus, C.3    Riguera, R.4
  • 67
    • 0037009990 scopus 로고    scopus 로고
    • For recent synthesis of polycyclic indoles, see: (a)
    • For recent synthesis of polycyclic indoles, see: (a) Kusama, H.; Takaya, J.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 11592-11593.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 11592-11593
    • Kusama, H.1    Takaya, J.2    Iwasawa, N.3
  • 70
    • 70249118843 scopus 로고    scopus 로고
    • For the preparation of 11, see the Supporting Information
    • For the preparation of 11, see the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.