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One‐Pot Tandem Cyclization of β‐Oxoamides, Primary Amines, and 3‐bromo‐1,1,1‐trifluoroacetone: Synthesis of 2/4‐trifluoromethyl‐substituted dihydropyrrol‐2/4‐ols
Author(s) -
Kishore Koppadi Syam Venkata,
Wasekar Chandrakant,
Borkar Prashant G.,
Shelke Mangesh E.,
Bansod Sudhakar,
Nechipadappu Sunil Kumar,
Shanker P. Sathya,
Dadmal Tulshiram L.
Publication year - 2025
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202401513
Subject(s) - chemistry , trifluoromethyl , tandem , primary (astronomy) , medicinal chemistry , combinatorial chemistry , organic chemistry , alkyl , materials science , physics , astronomy , composite material
Abstract A facile one‐pot, three‐component cascade cyclization has been developed for synthesis of 2‐trifluoromethyl‐2‐ol dihydropyrroles and 4‐trifluoromethyl‐4‐ol dihydropyrroles from various substituted amines, 3‐bromo‐1,1,1‐trifluoropropan‐2‐one, and substituted β‐oxoamides using K 2 CO 3 as an additive. This K 2 CO 3 ‐promoted method offers a simple and efficient approach for achieving highly regioselective products through cascade bond formation and cyclization. Post functionalization of resulting products into various valuable trifluoromethylated heterocycles including triazoles, isoxazoles, Mannich bases and the products from Sonogashira coupling reactions has also been reported. Additionally, a straightforward and scalable protocol for synthesis of 4‐trifluoromethylpyrrole‐3‐carboxamide derivatives without K 2 CO 3 , utilizing diverse 1,3‐dicarbonyl compounds has been established. This method demonstrates broad substrate compatibility, efficient tolerance towards a wide range of functional groups, making it a versatile strategy for accessing highly substituted trifluoromethylated pyrroles.
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