Preparation of Functional Benzofurans, Benzothiophenes, and Indoles Using Ester, Thioester, and Amide via Intramolecular Wittig Reactions

Preparation of new types of highly functional benzofurans, benzothiophenes, and indoles is realized via intramolecular Wittig reactions with the corresponding ester, thioester, and amide functionalities. The key intermediates, phosphorus ylides, presumably result from the addition of Bu3P toward ald...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 13; no. 11; pp. 2970 - 2973
Main Authors Syu, Siang-en, Lee, Yu-Ting, Jang, Yeong-Jiunn, Lin, Wenwei
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.06.2011
Amer Chemical Soc
Subjects
Aldehydes - chemical synthesis
Amides - chemistry
Benzene Derivatives - chemical synthesis
Benzene Derivatives - chemistry
Benzofurans - chemical synthesis
Benzofurans - chemistry
Chemistry
Chemistry, Organic
Esters
Indoles - chemical synthesis
Indoles - chemistry
Molecular Structure
Physical Sciences
Science & Technology
Thiophenes - chemical synthesis
Thiophenes - chemistry
REARRANGEMENT
POTENT
CATALYZED DIRECT
HETEROCYCLES
EFFICIENT SYNTHESIS
H BOND FUNCTIONALIZATION
ALKYNES
Online AccessGet full text

Cover

More Information
Summary:Preparation of new types of highly functional benzofurans, benzothiophenes, and indoles is realized via intramolecular Wittig reactions with the corresponding ester, thioester, and amide functionalities. The key intermediates, phosphorus ylides, presumably result from the addition of Bu3P toward aldehydes followed by acylation and deprotonation. Synthesis of functional benzofurans directly starting from salicylic aldehyde derivatives with acid chlorides in a one-step procedure is also developed.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol201062r