Premium
Cyclization of thiosemicarbazide derivative: As a source of novel synthesis of some azoles and azines
Author(s) -
Abd ElAzim Mohamed H. M.,
Assy Mohamed G.,
Khalil Mohammed I.,
Selim Yasser A.
Publication year - 2020
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.4022
Subject(s) - chemistry , ethyl bromoacetate , benzoyl chloride , chloroacetyl chloride , derivative (finance) , acylation , pyrazole , medicinal chemistry , phthalic anhydride , thiourea , ethyl acetoacetate , pyridazine , acetic anhydride , maleic anhydride , organic chemistry , chloride , polymer , copolymer , financial economics , economics , catalysis
In our study, we aimed to synthesize novel, some biologically active compounds, Azoles and Azines derivatives, that to be nitrogen‐containing heterocycles, and have their diverse therapeutic values. Thiosemicarbazide, 2 , was obtained from the attack of nitrogen of hydrazine to the carbon of heteroallene function of compound 1. Triazolotriazole derivative, 4 , was obtained from the reaction of 2 with diethyl malonate. Cyclization of thiourea unit of compound 2 with heteroallene, 1 , gave trazine, 6 . Benzolyation of 2 using benzoyl chloride formed triazole derivative, 8 . Reaction of 2 and maleic anhydride gave furothiadazine, 10. Cyclohexanopyrimidinthione, 12 , was obtained from cyclocondensation of cyclohexanone with 2. Triazole, 14 , was obtained from 2 and ammonium isothiocynate under thermal condition. Reaction of 2 with ethyl bromoacetate gave thiazole derivative, 16. [2+3] Cyclocondensation of acetyl acetone with 2 provided pyrazole, 18 . Triazolotriazole, 20 , was obtained from formalin and 2. Compound 2 suffers intramolecular base mediated cyclization affording pyrazole, 21. Keeping 2 and propinaldehyde under reflux provided triazolotriazole, 24. Acylation of 2 by succinic acid formed pyridazine derivative, 27.