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Improved Erlenmeyer Synthesis with 5‐Thiazolone and Catalytic Mn(II) Acetate. Crystal Structure Confirmation of the Reaction Stereochemistry
Author(s) -
Chandrasekhar Sosale,
Mohana Rao V.
Publication year - 2014
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.1921
Subject(s) - chemistry , erlenmeyer flask , catalysis , reagent , crystal structure , single crystal , aromaticity , organic chemistry , medicinal chemistry , molecule , crystallography
2‐Phenylthiazolin‐5‐one ( 5 , a thioazlactone) condenses with various aldehydes in the presence of the mild base Mn(II) acetate as catalyst in CH 2 Cl 2 solution. This leads to the corresponding Erlenmeyer reaction products ( 6 ) in excellent yields in the case of aromatic aldehydes and moderate yields in others. The mildness of the reaction conditions is apparently enabled by the aromaticity of the (putative) intermediate thiazolone anion. The structure and stereochemistry ( Z ) of the product derived from i ‐BuCHO was confirmed by single crystal X‐ray diffraction. This study overcomes key limitations of the classical Erlenmeyer synthesis and also introduces the relatively nontoxic Mn(II) acetate as a reagent in heterocyclic chemistry.