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Synthesis of (4 Z )‐4‐(Arylmethylidene)‐5‐ethoxy‐1,3‐oxazolidine‐2‐thiones by the Reaction of Ethyl (2 Z )‐3‐Aryl‐2‐isothiocyanatoprop‐2‐enoates with Organolithium Compounds
Author(s) -
Kobayashi Kazuhiro,
Ezaki Kosuke,
Hashimoto Hiroo
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.201200479
Subject(s) - chemistry , oxazolidine , alkoxy group , aryl , lithium (medication) , organolithium compounds , organic chemistry , medicinal chemistry , alkyl , ion , medicine , deprotonation , endocrinology
A convenient one‐pot method for the preparation of (4 Z )‐4‐(arylmethylidene)‐5‐ethoxy‐1,3‐oxazolidine‐2‐thiones 2 and 3 from ethyl (2 Z )‐3‐aryl‐2‐isothiocyanatoprop‐2‐enoates 1 , which can be easily prepared from ethyl 2‐azidoacetate and aromatic aldehydes, has been developed. Thus, these α ‐isothiocyanato α , β ‐unsaturated esters were treated with organolithium compounds, including lithium enolates of acetates, to provide 5‐substituted (4 Z )‐4‐(arylmethylidene)‐5‐ethoxy‐1,3‐oxazolidine‐2‐thiones, 2 , and 2‐[(4 Z )‐(4‐arylmethylidene)‐5‐ethoxy‐2‐thioxo‐1,3‐oxazolidin‐5‐yl]acetates, 3 .