Document Detail

Synthesis of new 2-vinylation products of indole via a Michael-type addition reaction with dimethyl acetylenedicarboxylate and their Diels-Alder reactivity as precursors of new carbazoles.
MedLine Citation:
PMID:  16995688     Owner:  NLM     Status:  MEDLINE    
Reaction of 4,7-dihydroindole and dimethyl acetylenedicarboxylate provided a convenient route to functionalized 2-vinylindoles. Diels-Alder reactions of the 2-vinylindoles with naphthoquinone, p-benzoquinone, 1,2-dicyano-4,5-dichloroquinone, N-phenyltriazolinedione, and tetracyanoethylene were investigated to give [c]annelated 1,2-dihydro, 1,2,3,4-tetrahydro, and fully aromatized carbazoles. The structure and formation mechanism of both 2-vinylindoles and their cycloadduct are discussed.
Hüseyin Cavdar; Nurullah Saraçoglu
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  71     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2006 Sep 
Date Detail:
Created Date:  2006-09-25     Completed Date:  2007-07-25     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  7793-9     Citation Subset:  IM    
Department of Chemistry, Atatürk University, 25240 Erzurum, Turkey.
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MeSH Terms
Carbazoles / chemical synthesis*,  chemistry
Carboxylic Acids / chemistry
Indoles / chemistry
Molecular Structure
Vinyl Compounds / chemical synthesis*
Reg. No./Substance:
0/Carbazoles; 0/Carboxylic Acids; 0/Indoles; 0/Vinyl Compounds

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