Synthesis of 2‐Aminothiazole Derivatives in Easy Two‐Step, One‐Pot Reaction

Synthesis of 2‐Aminothiazole Derivatives in Easy Two‐Step, One‐Pot Reaction Condensation of brominated ethyl acetoacetate with thiourea gives 2‐amino‐5‐ethoxycarbonyl‐4‐methylthiazole (1) and ethyl α‐(2‐amino‐4‐thiazolyl)acetate (2), indicating that bromination of the substrate occurs on both sides of the carbonyl group. X‐ray diffraction studies indicate weak hydrogen bonds of the amino groups, which are not observed in the IR spectra. The 1 molecule adopts planar S,O‐anti conformation in the crystal lattice, whereas the methylene group, insulating thiazole ring and the ester group in 2 molecule, makes it more flexible and makes the ester group nearly perpendicular to the thiazole ring. The small deviations of the bond lengths and angles indicate mesomeric interaction between complementary substituents across the thiazole ring. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Journal of Heterocyclic Chemistry Wiley

Synthesis of 2‐Aminothiazole Derivatives in Easy Two‐Step, One‐Pot Reaction

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Publisher
Wiley Subscription Services, Inc., A Wiley Company
Copyright
© 2018 Wiley Periodicals, Inc.
ISSN
0022-152X
eISSN
1943-5193
D.O.I.
10.1002/jhet.3086
Publisher site
See Article on Publisher Site

Abstract

Condensation of brominated ethyl acetoacetate with thiourea gives 2‐amino‐5‐ethoxycarbonyl‐4‐methylthiazole (1) and ethyl α‐(2‐amino‐4‐thiazolyl)acetate (2), indicating that bromination of the substrate occurs on both sides of the carbonyl group. X‐ray diffraction studies indicate weak hydrogen bonds of the amino groups, which are not observed in the IR spectra. The 1 molecule adopts planar S,O‐anti conformation in the crystal lattice, whereas the methylene group, insulating thiazole ring and the ester group in 2 molecule, makes it more flexible and makes the ester group nearly perpendicular to the thiazole ring. The small deviations of the bond lengths and angles indicate mesomeric interaction between complementary substituents across the thiazole ring.

Journal

Journal of Heterocyclic ChemistryWiley

Published: Jan 1, 2018

References

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