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Studies on the synthesis of heterocyclic compounds. Synthesis of 1,3,2‐benzoxathia‐ and 1,3,2‐benzodioxastibole derivatives
Author(s) -
Anchisi Carlo,
Corda Luciano,
Maccioni Antonio,
Podda Gianni,
Cabiddu Salvatore
Publication year - 1976
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.5570130519
Subject(s) - chemistry , triethylamine , sodium ethoxide , antimony , pyridine , sodium hydroxide , halogen , medicinal chemistry , organic chemistry , alkyl , ethanol
Abstract The preparation of 1,3,2‐benzoxathia‐ and 1,3,2‐benzodioxachlorostiboles (IIa‐b) by reaction of antimony trichloride with 2‐hydroxythiophenol (Ia) or 1,2‐benzodiol (Ib) is described. The halogen was easily removed. Thus a Wurtz‐like reaction gave the distibole compounds (IVa‐b), which were also produced by organolithium compounds or pyridine. The compounds Va‐b were obtained with sodium hydroxide, ethoxide and phenoxide, but spiran derivatives VIIa‐b, of antimony, were obtained by treating IIa‐b with 2‐hydroxythiophenol or 1,2‐benzodiol in the presence of triethylamine. The structure of the prepared compounds was determined by spectro‐scopic methods.