Improved Erlenmeyer Synthesis with 5-Thiazolone and Catalytic Mn(II) Acetate. Crystal Structure Confirmation of the Reaction Stereochemistry
Publication type: Journal Article
Publication date: 2014-04-18
scimago Q3
wos Q2
SJR: 0.362
CiteScore: 4.7
Impact factor: 2.4
ISSN: 0022152X, 19435193
Organic Chemistry
Abstract
2-Phenylthiazolin-5-one (5, a thioazlactone) condenses with various aldehydes in the presence of the mild base Mn(II) acetate as catalyst in CH2Cl2 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.
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Chandrasekhar S., Mohana Rao V. Improved Erlenmeyer Synthesis with 5-Thiazolone and Catalytic Mn(II) Acetate. Crystal Structure Confirmation of the Reaction Stereochemistry // Journal of Heterocyclic Chemistry. 2014. Vol. 51. No. S1. p. E172-E175.
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Chandrasekhar S., Mohana Rao V. Improved Erlenmeyer Synthesis with 5-Thiazolone and Catalytic Mn(II) Acetate. Crystal Structure Confirmation of the Reaction Stereochemistry // Journal of Heterocyclic Chemistry. 2014. Vol. 51. No. S1. p. E172-E175.
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TY - JOUR
DO - 10.1002/jhet.1921
UR - https://doi.org/10.1002/jhet.1921
TI - Improved Erlenmeyer Synthesis with 5-Thiazolone and Catalytic Mn(II) Acetate. Crystal Structure Confirmation of the Reaction Stereochemistry
T2 - Journal of Heterocyclic Chemistry
AU - Chandrasekhar, Sosale
AU - Mohana Rao, V
PY - 2014
DA - 2014/04/18
PB - Wiley
SP - E172-E175
IS - S1
VL - 51
SN - 0022-152X
SN - 1943-5193
ER -
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@article{2014_Chandrasekhar,
author = {Sosale Chandrasekhar and V Mohana Rao},
title = {Improved Erlenmeyer Synthesis with 5-Thiazolone and Catalytic Mn(II) Acetate. Crystal Structure Confirmation of the Reaction Stereochemistry},
journal = {Journal of Heterocyclic Chemistry},
year = {2014},
volume = {51},
publisher = {Wiley},
month = {apr},
url = {https://doi.org/10.1002/jhet.1921},
number = {S1},
pages = {E172--E175},
doi = {10.1002/jhet.1921}
}
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MLA
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Chandrasekhar, Sosale, and V Mohana Rao. “Improved Erlenmeyer Synthesis with 5-Thiazolone and Catalytic Mn(II) Acetate. Crystal Structure Confirmation of the Reaction Stereochemistry.” Journal of Heterocyclic Chemistry, vol. 51, no. S1, Apr. 2014, pp. E172-E175. https://doi.org/10.1002/jhet.1921.