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Current Organic Synthesis


ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

Synthesis and Characterization of Poly([1,2,4]triazolyl- and [1,2,4]triazolo[3,4- b][1,3,4]thiadiazinylsulfanylmethyl)arenes: Novel Multi-Armed Molecules.

Author(s): Ahmed H. M. Elwahy, Radwan M. Sarhan and Mohamed A. Badawy

Volume 10, Issue 5, 2013

Page: [786 - 790] Pages: 5

DOI: 10.2174/1570179411310050008

Price: $65


A synthesis of novel three-, four-, and sixfold branched triazoles 3-5 and triazolothiadiazines 7, 8 and 10, which are linked to a benzene core via sulfanylmethylene spacers was reported. The reaction proceeded via initial treatment of the appropriate poly(bromomethyl)arenes 2 with the corresponding equivalents of 4-amino-4H-1,2,4-triazoles 1 in refluxing ethanolic KOH to give poly(triazolyl)arenes 3-5. Subsequent reaction of 4b and 5b with phenacyl bromide in refluxing DMF-ethanol mixture afforded poly(triazolothiadiazinyl)arenes 7 and 8, respectively. Compounds 7 and 8 were alternatevely obtained by the reaction of 2b and 2c with 6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine-3-thiol 9 in refluxing EtOH/DMF containing KOH. Similarly, threefold substitution of 2a with three equivalents of 9 afforded 10 in good yield.

Keywords: Poly(bromomethyl)arenes, alkylation, cyclization, triazoles, triazolo-thiadiazines.

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