Synthesis of Azirinyl Ethynyl Ketones and Their Use in the Preparation C(O)C≡CR-Substituted NH-Pyrroles/NH-Imidazoles and Azole–Azine/Azole–Azole Heterocyclic Hybrids

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 24, 2025

Azirinyl-substituted conjugated ynones were first synthesized by the reaction of lithiated acetylenes with 2H-azirine-2-carbonyl chlorides. Azirinyl ethynyl ketones containing only a C(O)C≡CR substituent at position 2 azirine ring are good precursors for obtaining α-C(O)C≡CR substituted NH-pyrroles and 5-[C(O)C≡CR]-substituted NH-imidazoles, reacting selectively moiety 1,3-diketones arylamidines, respectively. Various N-heterocyclic hybrids (pyrrole-pyrimidine, imidazole-pyrimidine, pyrrole-isoxazole, imidazole-isoxazole, pyrimidine-pyrrole-thiophene, pyrrole-pyrimidine-thiophene, imidazole-pyrimidine-thiophene, isoxazole-pyrrole-thiophene) have been prepared based on orthogonal or domino reactions an moieties azirinyl ketones.

Language: Английский

Azirine Weinreb amides: preparation and use in the synthesis of 2-acylated aziridines and azirines

Tetrahedron, Journal Year: 2024, Volume and Issue: 167, P. 134255 - 134255

Published: Sept. 6, 2024

Language: Английский