Synthesis of benzothiophene and indole derivatives through metal-free propargyl-allene rearrangement and allyl migration

An efficient base-catalyzed protocol for the synthesis of benzothiophene is described. The reaction proceeds via base-promoted propargyl-allenyl rearrangement followed by cyclization and allyl migration. Phosphine-substituted indoles can be synthesized by a similar strategy.

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Bibliographic Details
Published inBeilstein journal of organic chemistry Vol. 13; no. 1; pp. 1866 - 1870
Main Authors Yao, Jinzhong, Xie, Yajie, Zhang, Lianpeng, Li, Yujin, Zhou, Hongwei
Format Journal Article
LanguageEnglish
Published Germany Beilstein-Institut zur Föerderung der Chemischen Wissenschaften 06.09.2017
Beilstein-Institut
Subjects
allyl migration
benzothiophene
Chemistry
Full Research Paper
indole
Indoles
metal-free
Migration
Natural products
Phosphine
propargyl-allenyl
benzothiophene
allyl migration
indole
metal-free
propargyl-allenyl
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Summary:An efficient base-catalyzed protocol for the synthesis of benzothiophene is described. The reaction proceeds via base-promoted propargyl-allenyl rearrangement followed by cyclization and allyl migration. Phosphine-substituted indoles can be synthesized by a similar strategy.
Bibliography:ObjectType-Article-1
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content type line 23
ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.13.181