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Volumn 16, Issue 7, 2010, Pages 2031-2035

A facile one-pot transformation of baylis-hillman adducts into unsymmetrical disubstituted maleimide and maleic anhydride frameworks: A facile synthesis of himanimide A

Author keywords

Friedel crafts reaction; Heterocycles himanimide a; Natural products; Synthetic methods

Indexed keywords

BAYLIS-HILLMAN ADDUCTS; BIOACTIVE COMPOUNDS; CHEMICAL EQUATIONS; FACILE SYNTHESIS; HETEROCYCLES; MALEIMIDES; NATURAL PRODUCTS; ONE POT; SYNTHETIC METHODS; UNSYMMETRICAL;

EID: 76449088834     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200902887     Document Type: Article
Times cited : (37)

References (95)
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    • For leading references on Friedel-Crafts reactions with B-H adducts/derivatives, see: a
    • For leading references on Friedel-Crafts reactions with B-H adducts/derivatives, see: a) C. G. Lee, K. Y. Lee, S. Lee, J. N Kim, Tetrahedron 2005, 61, 1493-1499;
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    • The B-H alcohols 1a-m, 5, and 6 a-e were prepared following the known procedure, see: D. Basavaiah, T. K. Bharathi, V. V. L. Gowriswari, Tetrahedron Lett. 1987,28, 4351-4352.
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    • These derivatives are named as 3,4-disubstituted maleimide and maleic anhydride derivatives according to the following numbering
    • These derivatives are named as 3,4-disubstituted maleimide and maleic anhydride derivatives according to the following numbering:
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    • We cannot completely rule out the formation of minor amounts of fumaric acid derivatives in these reactions, since the yields of maleimide are not quantitative and also the yields of maleic anhydride derivatives are low.
    • We cannot completely rule out the formation of minor amounts of fumaric acid derivatives in these reactions, since the yields of maleimide are not quantitative and also the yields of maleic anhydride derivatives are low.
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    • Detailed X-ray crystallographic data for compounds 2 a (CCDC687372), 2e (CCDC-687373), 2k (CCDC-687374), 7a (CCDC687375) can be obtained free of charge from The Cambridge Crystallographic Data Centre via
    • Detailed X-ray crystallographic data for compounds 2 a (CCDC687372), 2e (CCDC-687373), 2k (CCDC-687374), 7a (CCDC687375) 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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    • During the course of the Friedel-Crafts reaction, the t-butyldimethylsilyl protecting group was cleaved to provide the corresponding phenol derivative (2n).
    • During the course of the Friedel-Crafts reaction, the t-butyldimethylsilyl protecting group was cleaved to provide the corresponding phenol derivative (2n).
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    • We also noticed that longer reaction times gave a mixture of products as evidenced by TLC examination.
    • We also noticed that longer reaction times gave a mixture of products as evidenced by TLC examination.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.