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Volumn 351, Issue 7-8, 2009, Pages 1073-1079

Synthesis of 2,6-dioxo-1,2,3,4,5,6-hexahydroindoles by acid-catalyzed cyclization of acetal-protected (2,4-dioxocyclohex-l-yl)acetamides and their transformation into 5,8,9,10-tetrahydro-6H-indolo[2,1-a]isoquinolin-9-ones

Author keywords

Alkaloids; Amides; C C bond formation; Cyclization; Nitrogen heterocycles

Indexed keywords


EID: 66149158122     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800691     Document Type: Article
Times cited : (16)

References (35)
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    • For other syntheses of 2,6-dioxo-1,2,3,4,5,6-hexahy-droindoles, see: a Birch reaction: K. Ito, M. Haruna, H. Furukawa, J. Chem. Soc. Chem. Commun. 1975, 681;
    • For other syntheses of 2,6-dioxo-1,2,3,4,5,6-hexahy-droindoles, see: a) Birch reaction: K. Ito, M. Haruna, H. Furukawa, J. Chem. Soc. Chem. Commun. 1975, 681;
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    • aza-Claisen rearrangement of isoquinuclidines: Y. Chen, P. L. Huesmann, P. S. Mariano, Tetrahedron Lett. 1983, 24, 1021;
    • b) aza-Claisen rearrangement of isoquinuclidines: Y. Chen, P. L. Huesmann, P. S. Mariano, Tetrahedron Lett. 1983, 24, 1021;
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    • Diels-Alder reaction of 2-imido-furans: A. Padwa, J. D. Ginn, J. Org. Chem. 2005, 70, 5197;
    • c) Diels-Alder reaction of 2-imido-furans: A. Padwa, J. D. Ginn, J. Org. Chem. 2005, 70, 5197;
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    • and references cited therein. For a recent review of dianions, see
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    • CCDC 716534, CCDC 670738, and CCDC 716346 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data-request/cif.
    • CCDC 716534, CCDC 670738, and CCDC 716346 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data-request/cif.
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    • We have prepared 7c by oxidation of 2-allylcyclohexa-none (5c) which is readily available from cyclohexa-none see below, This approach to 7c has, to the best of our knowledge, not yet been reported. For a different synthesis of 7c, see for example: S. M. Allin, S. L. James, M. R. Elsegood, W. P. Martin, J. Org. Chem. 2002, 67, 9464
    • We have prepared 7c by oxidation of 2-allylcyclohexa-none (5c) which is readily available from cyclohexa-none (see below). This approach to 7c has, to the best of our knowledge, not yet been reported. For a different synthesis of 7c, see for example: S. M. Allin, S. L. James, M. R. Elsegood, W. P. Martin, J. Org. Chem. 2002, 67, 9464.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.