53324-02-0Relevant articles and documents
Synthesis of some heterocycles of expected biological activity through the action of isatin-3-thiosemicarbazone on acetylenic ketones and esters
Youssef, Ahmed S. A.
, p. 173 - 188 (2007/10/03)
Isatin-3-thiosemicarbazone (1) reacted with 1-aryl-3-phenylprop-2-yn-1-ones (2a-c) in n-butanol to give 4-aryl-6-phenyl-2-[2-oxo-2H,3H-benzo(b) pyrrolidine-3-iminyl]-imino-2H-1,3-thiazines (3a-c). Similar treatment of 1 with acetylenic esters (4a-c) gave the 6-substituted derivatives of 2-imino-3-[2-oxo-2H,3H-benzo(b)pyrrolidine-3-iminyl]-2,3-dihydro-4-oxo-1,3- thiazine (5a-c). Treatment of 1 with 4a-c in the presence of sodium ethoxide in ethanol gave the 6-substituted derivatives of 3-[2-oxo-2H,3H-benzo(b)pyrrolidine-3-iminyl]-4-oxo-2-thioxo-1,2,4- trihydropyrimidine (6a-c). However, when 1 was refluxed with 1-p-chlorophenyl-3-phenylprop-2-yn-1-one (2b) in ethanol it gave a mixture of 2,4,6-tris[2-oxo-2H,3H-benzo(b)pyrrolidine-3-iminyl] amino-1,3,5-triazine (7) and Z,Z-3,3′-thiodi(1-p-chlorophenyl-3-phenylprop-2-en-1-one) (8). The aziridine imine derivative (9) and the pyrazole derivatives (10a and b) were the only isolated products upon treatment of 3c, 6a, and 6c and 3a and 3b with hydrazine hydrate, respectively. Structures of all new compounds are evidenced by microanalytical and spectral data.
