One‐pot synthesis of polyfunctionally substituted 2,3‐dihydrothiazoles and thiazolidinones

Abstract

The reaction of phenyl isothiocyanate with the active methylene reagents 1a–e gives the nonisolable 1:1 adducts 2a–e. The latter react with α‐halogenated compounds, e.g. phenacyl bromide, bromoacetyl bromide, chloroacetone, chloroacetonitrile and some hydrazonoyl halides to give the corresponding polyfunctionally substituted 2,3‐dihydrothiazoles or thiazolidinone ring systems.

Synthesis and antibacterial activity of some new heterocycles incorporating phthalazine

“…The remarkable importance of a-bromoacetonitrile derivatives [14,15], for the construction of variety of heterocyclic compounds promoted us to investigate the synthesis of new bromopropionitrile derivative. Thus, a suspension of 1 in acetic acid or chloroform reacted readily with bromine to yield dibromopropionitrile derivative 9, while monobromopropionitrile derivative 10 was not obtained, but when the reaction take place with N-bromosuccinamide in dimethylformamide at room temperature compound 9 was obtained.…”

Spectroscopic study of the keto-enol equilibrium of N-aryldiacetylthioacetamides and their reactivity

“…Due to this exceptionally polyfunctional character of compound 1 [9], its reactivity may have a wide synthetic potential.…”

Synthesis and reactions of indane‐1,3‐dione‐2‐thiocarboxanilides with hydrazonoyl halides and active chloromethylene compounds

“…This finding influenced us to investigate the reaction of 5 with active chloromethylene compounds 15a-d to see if such reactions will lead to thiazolines and/or 1,3-oxathioles. Previous literature reports indicated that reactions of ␣-halo derivatives of simple ketones and esters with potassium salts of acyclic thioamides [2,3,9] afforded the thiazolines and/or 1,3-oxathioles [10].…”

“…Recently, it was indicated that the reactions of C-acyl-Narylnitrilimines with active methine thioanilides yield the corresponding thiazoline derivatives [2,3]. More recently, Hassaneen et al reported that hydrazonoyl halides 1 and 2 reacted with thioanilides to give the corresponding thiadiazoles via elimination of the arylamine moiety [4][5][6].…”