Premium
Synthesis and Structures of Novel Multi‐armed Molecules Involving Benzene as a Core and 4‐Phenylthiazole, 4‐Pyrazolylthiazole, or Thiadiazole Units as Arms
Author(s) -
Salem Mostafa E.,
Darweesh Ahmed F.,
Farag Ahmad M.,
Elwahy Ahmed H. M.
Publication year - 2017
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.2629
Subject(s) - chemistry , benzene , aldehyde , acetic anhydride , condensation , ethanol , molecule , acetic acid , condensation reaction , medicinal chemistry , organic chemistry , catalysis , combinatorial chemistry , physics , thermodynamics
A synthesis of novel three‐, four‐, and sixfold branched 4‐phenylthiazolylhydrazones, 4‐pyrazolylthiazolyl hydrazones, and thiadiazoles which are linked to a benzene core via phenoxymethyl spacers was reported. The synthetic methodology includes initially formation of poly(aldehyde thiosemicarbazones) 9 , 14 , and 15 by acid catalyzed condensation of thiosemicarbazide ( 8 ) with the appropriate poly(aldehydes) 3 , 5 , and 7 , respectively. Subsequent reaction of 9 , 14 , and 15 with each of 2‐bromo‐1‐phenylethanone ( 10a ) and 2‐bromo‐1‐( 4 ‐chlorophenyl)ethanone ( 10b ) in refluxing ethanol in the presence of few drops of TEA afforded 11 , 16 , and 18 , respectively, in good yields. On the other hand, the synthesis of the novel poly(4,5‐dihydro‐1,3,4‐thiadiazolyl) derivatives 20 , 21a , 21b , and 22 was performed by cyclization of 9b , 14a , 14b , and 15a , respectively, in refluxing acetic anhydride .