Rhodium-Catalyzed Synthesis of Isoquinolines and Indenes from Benzylidenehydrazones and Internal Alkynes

A new route is presented for the selective assembly of isoquinolines and indenes by rhodium-catalyzed tandem cyclization of benzylidenehydrazones with internal alkynes. This method involves the selective cleavage of the N–N bond and the CN bonds and is dependent on the substituents of the benzylide...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 79; no. 3; pp. 1025 - 1031
Main Authors Huang, Xiao-Cheng, Yang, Xu-Heng, Song, Ren-Jie, Li, Jin-Heng
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.02.2014
Amer Chemical Soc
Subjects
Alkynes - chemistry
Catalysis
Chemistry
Chemistry, Organic
Hydrazines - chemistry
Indenes - chemical synthesis
Indenes - chemistry
Isoquinolines - chemical synthesis
Isoquinolines - chemistry
Molecular Structure
Physical Sciences
Rhodium - chemistry
Science & Technology
H BOND ACTIVATION
3+2 ANNULATION
AROMATIC KETIMINES
CYCLOADDITION REACTIONS
N-AZIRIDINYLIMINES
ONE-POT SYNTHESIS
REGIOSELECTIVE SYNTHESIS
DIAZO-COMPOUNDS
CONTAINING HETEROCYCLES
C-H
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Summary:A new route is presented for the selective assembly of isoquinolines and indenes by rhodium-catalyzed tandem cyclization of benzylidenehydrazones with internal alkynes. This method involves the selective cleavage of the N–N bond and the CN bonds and is dependent on the substituents of the benzylidenehydrazone.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo402497v