83570-69-8Relevant academic research and scientific papers
Reaction of Hydrazidoyl Halides with Thiocyanate Anion: Synthesis of Thiadiazolines and Thiadiazoloquinazoline
Ibrahim, Mohamed Kamal Ahmed
, p. 120 - 122 (2007/10/02)
Hydrazidoyl chlorides (1a-d) react with potassium thiocyanate to give 5-imino-Δ2-1,3,4-thiadiazoline derivatives (4a-d).The corresponding N-acetyl-, N-benzoyl- and N-ethoxycarbonyl-thiadiazolines (5, 6 and 7) have been obtained via 1,3-dipolar cycloaddition of 1d to acetyl isothiocyanate, benzoyl isothiocyanate and ethoxycarbonyl isothiocyanate or via acylation reaction of compound 4d with acetyl chloride, benzoyl chloride and ethyl chloroformate.Compound 1e, however, on reaction with potassium thiocyanate furnishes directly the thiadiazoloquinazoline (8).Condensation of 4a with α-halogenketones and isothiocyanates gives N-alkylderivatives (9-11) and thioureas (12-14) respectively.Compound 4c on treatment with nitrous acid followed by reduction gives hydrazine derivative (16) via the intermediate 15.Bromination of 4b furnishes 17 which on reaction with cyanide ion furnishes the corresponding cyanoacetyl derivative (18).
FACILE SYNTHESIS OF THIADIAZOLO QUINAZOLINE DERIVATIVES VIA THE JAPP-KLINGEMANN REACTION
Abdelhamid, Abdou O.,Hassaneen, Hamdi M.,Abbas, Ikhlass M.,Shawali, Ahmad S.
, p. 1527 - 1530 (2007/10/02)
Diazotized anthranilic acid and its methyl ester react with substituted α-thiocyanatoacetoacetanilides 3a-c to give in both cases the corresponding thiadiazolo quinazolines 6a-c, respectively.A mechanism is proposed and it is substantiated by synthesis of 6a from N-(2-carboxyphenyl)-C-phenylcarbamoyl hydrazidoyl chloride 8a or its N-(2-methoxycarbonylcarbonylphenyl) analogue 8d.
