Formation of 1,3,4-Oxadiazoles by Cyclisation of Acetoacetanilide Acylhydrazones under Mild Conditions

Dzvinchuk, I. B.; Kartashov, S. A.; Lozinskii, M. O.; Русанов, Эдуард Б.; Chernega, Alexander N.

doi:10.3184/030823402103171221

Cited by 3 publications

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References 7 publications

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“…Dzvinchuk et al reported a synthesis of substituent 1,3,4‐oxadiazoles 180 by the acidic cyclization of acetoacetanilide acylhydrazones 178 . Heating 178 in Ac 2 O/TFA (v/v = 10/1) at 40–50 °C for 2–5 h, the enamine form 179 automatically cyclized to 180 in 55%–97% yields (Scheme 47) [91].…”

Section: Five‐membered Heterocycles Containing Multiple Heteroatomsmentioning

confidence: 99%

The applications of β‐keto amides for heterocycle synthesis

2022

Journal of Heterocyclic Chem

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β-Keto amides have multiple nucleophilic and electrophilic reaction sites within their molecular structures, which make them excellent building blocks for the construction of various heterocyclic compounds. In this Review, we summarized the applications of structurally diversified β-keto amides for the synthesis of (1) Five-membered heterocycles including furans, thiophenes, pyrroles, indoles, pyrazoles, triazoles, and their derivatives; (2) six-membered nitrogen-and oxygen-containing heterocycles such as pyridones, dihydropyridines, pyridines, quinolones, quinolines, pyranones and the like; (3) various lactams and some aza-aliphatic rings. The focus is on the multicomponent reactions which take advantage of the unique versatile reactivities of β-keto amides.

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Section: Five‐membered Heterocycles Containing Multiple Heteroatomsmentioning

confidence: 99%