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Synthesis of 2, N , N ‐Trisubstituted 1 H ‐Indole‐1‐carbothioamides from 2‐(Acylmethyl)phenyl Isocyanides
Author(s) -
Kobayashi Kazuhiro,
Yamane Kazuya,
Fukamachi Shuhei
Publication year - 2013
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201200236
Subject(s) - chemistry , thiourea , indole test , alkyl , medicinal chemistry , combinatorial chemistry , organic chemistry
A convenient procedure for the synthesis of 2, N , N ‐trisubstituted 1 H ‐indole‐1‐carbothioamides from 2‐(acylmethyl)phenyl isocyanides has been developed. Thus, these isocyanides are converted into ( Z )‐ [1‐alkyl (or phenyl)‐2‐(2‐isothiocyanatophenyl)ethenyl] 1,1‐dimethylethyl carbonates via an easy two‐step sequence. Treatment with secondary amines gave thiourea intermediates which afforded with CF 3 COOH (TFA) the desired products in fair‐to‐good yields.