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Synthesis of 2‐methylthioindolizine‐3‐carbonitriles using nitro ketene dithioacetal
Author(s) -
Tominaga Yoshinori,
Shiroshita Yoshihide,
Hosomi Akira
Publication year - 1988
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570250627
Subject(s) - chemistry , ketene , triethylamine , thio , medicinal chemistry , bromide , organic chemistry , nitro , azine , alkyl
The reaction of 1‐cyanomethylpyridinium chloride or bromide, 1a‐i , with 1,1‐bis(methylthio)‐2‐nitroethylene ( 2 ) in the presence of triethylamine as a base in ethanol gave the corresponding 2‐methylthioindolizine‐3‐carbonitrile 3 and 2‐methyl‐thio‐1‐nitroindolizine‐3‐carbonitrile 4 in good yields, respectively. Compounds 3a,f were key intermediates for the synthesis of cycl[3.2.2]azine derivatives.
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