Regioselectivity in Reactions of Bis‐Hydrazonoyl Halides with Some Bifunctional Heterocycles | Zendy

Shawali Ahmad S. | Zendy; Abdallah Magda A. | Zendy; Zayed Mohie E. M. | Zendy

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Regioselectivity in Reactions of Bis‐Hydrazonoyl Halides with Some Bifunctional Heterocycles

Author(s) -

Shawali Ahmad S.,

Abdallah Magda A.,

Zayed Mohie E. M.

Publication year - 2002

Publication title -

journal of the chinese chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.329

H-Index - 45

eISSN - 2192-6549

pISSN - 0009-4536

DOI - 10.1002/jccs.200200148

Subject(s) - chemistry , regioselectivity , bifunctional , medicinal chemistry , halide , chloride , pyrimidinones , derivative (finance) , combinatorial chemistry , organic chemistry , catalysis , financial economics , economics

Bis‐hydrazonoyl chloride 1 reacts regioselectively with 3‐mercapto‐1,2,4‐triazole 2a , 2,3‐dihydro‐3‐thioxo‐1,2,4‐triazin‐5(4H)‐one 2b and 2‐mercaptobenzimidazole 2c to give the hitherto unknown annelated 2,3‐bis‐(phenylhydrazono)thiazoles 6a‐c , respectively. Reactions of 1 with the methylthio derivatives of such heterocycles afforded the annelated 3,3′‐bis‐(1,2,4‐triazoles) 11a‐c , respectively. Similar reaction of 1 with 2‐phenylamino‐4(3H)‐pyrimidinones 4 gave 2,3‐bis(phenylhydrazono)imidazo[1,2‐a]pyrimidin‐5(1H)‐ones 16 . Oxidation of 6c yielded the corresponding bis(phenylazo) derivative 15 . The regiochemistry of the studied reactions is discussed.

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