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Synthesis of Polysubstituted 3‐Methylisoquinolines through the 6π‐Electron Cyclization/Elimination of 1‐Azatrienes derived from 1,1‐Dimethylhydrazine
Author(s) -
Vargas Didier F.,
Larghi Enrique L.,
Kaufman Teodoro S.
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801076
Subject(s) - chemistry , dimethylhydrazine , hydrazine (antidepressant) , aromatization , combinatorial chemistry , 1,2 dimethylhydrazine , silylation , organic chemistry , medicinal chemistry , catalysis , medicine , carcinogenesis , biochemistry , colorectal cancer , chromatography , cancer , azoxymethane , gene
A convenient one pot microwave‐assisted 6π‐electron cyclization/aromatization approach toward 3‐methylisoquinolines is reported. The starting 1‐azatriene derivatives were prepared in situ by reaction of 2‐propenylbenzaldehydes with 1,1‐dimethylhydrazine, which exhibited superior performance when compared with other hydrazine derivatives. Minor amounts of the related 3,4‐dihydro isoquinolines were formed concomitantly with the isoquinolines, and a mechanism for their generation was proposed. The reaction conditions were optimized, and its scope and limitations were explored. In general, the transformation proceeded in moderate to good yields.