Transition-Metal Catalyzed Rapid Synthesis of Imidiazo[2,1-b]thiazoles: Access to Aza-Fused Heterocycles via Aerobic Oxidative Coupling of 2-Aminothiazoles and Acetophenones

Publication typeJournal Article
Publication date2024-07-18
scimago Q2
wos Q2
SJR0.559
CiteScore4.6
Impact factor2.3
ISSN00397881, 1437210X
Abstract

We report an efficient synthesis of 6-substituted imidazo[2,1-b]thiazoles from 2-aminothiazoles and acetophenones through intramolecular cyclization of in situ generated thiazolium ylides. This one-pot cascade process efficiently forms two C–N bonds and is facilitated by both Cu(OTf)2/KI and FeCl3/ZnI2 systems. The method utilizes commercially available starting materials and features mild reaction conditions, tolerance to different functional groups, and ease of operation. The synthetic applicability has further been demonstrated through post-modification of imidazo[2,1-b]thiazole analogues.

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Basak S. J. et al. Transition-Metal Catalyzed Rapid Synthesis of Imidiazo[2,1-b]thiazoles: Access to Aza-Fused Heterocycles via Aerobic Oxidative Coupling of 2-Aminothiazoles and Acetophenones // Synthesis. 2024.
GOST all authors (up to 50) Copy
Dash J., Basak S. J., Paul P. Transition-Metal Catalyzed Rapid Synthesis of Imidiazo[2,1-b]thiazoles: Access to Aza-Fused Heterocycles via Aerobic Oxidative Coupling of 2-Aminothiazoles and Acetophenones // Synthesis. 2024.
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TY - JOUR
DO - 10.1055/a-2369-3893
UR - http://www.thieme-connect.de/DOI/DOI?10.1055/a-2369-3893
TI - Transition-Metal Catalyzed Rapid Synthesis of Imidiazo[2,1-b]thiazoles: Access to Aza-Fused Heterocycles via Aerobic Oxidative Coupling of 2-Aminothiazoles and Acetophenones
T2 - Synthesis
AU - Dash, Jyotirmayee
AU - Basak, Soumya Jyoti
AU - Paul, Pratap
PY - 2024
DA - 2024/07/18
PB - Georg Thieme Verlag KG
SN - 0039-7881
SN - 1437-210X
ER -
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@article{2024_Basak,
author = {Jyotirmayee Dash and Soumya Jyoti Basak and Pratap Paul},
title = {Transition-Metal Catalyzed Rapid Synthesis of Imidiazo[2,1-b]thiazoles: Access to Aza-Fused Heterocycles via Aerobic Oxidative Coupling of 2-Aminothiazoles and Acetophenones},
journal = {Synthesis},
year = {2024},
publisher = {Georg Thieme Verlag KG},
month = {jul},
url = {http://www.thieme-connect.de/DOI/DOI?10.1055/a-2369-3893},
doi = {10.1055/a-2369-3893}
}