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Alkyl Heteroaromatics as Building Blocks in Organic Synthesis: The Reactivity of Alkyl Azoles toward Electrophilic Reagents

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Alkyl Heteroaromatics as Building Blocks in Organic Synthesis:

The Reactivity of Alkyl Azoles toward Electrophilic Reagents

I. S. Abdel Hafiz

a

, A. A. Hassanien

a

, and A. M. Hussein

b,

*

a Department of Chemistry, Faculty of Education, Suez Canal University, Arish, Egypt

b Department of Chemistry, Faculty of Science, Al-Azhar University, Assiut 71524, Egypt

* Reprint requests to Dr. A. M. Hussein. Fax: 002 088 325436.

E-mail: haleemÐmÐh@hotmail.com

Z. Naturforsch.54b,923Ð928 (1999); received January 14, 1999

Oxazolone, Imidazolone, Oxazolopyridines, Pyridobenzoxazine, Thiazolone

Oxazolone(1)couples with aromatic diazonium salts to yield the arylhydrazones(3a-c).

Compound3reacts with aniline to give aryl hydrazone(5).Compound5was also obtained viaconverting1into the imidazolone(4)and subsequent treatment of4with aromatic diazo- nium salts. Compounds1and12reacted with arylidenemalononitrile(6)to yield compounds 8and14respectively. Also compounds1, 12condensed with an aromatic aldehydes to yield 11 and 17. Compounds 11, 17 reacted further with one molecule of malononitrile to give compounds 8 and 14,respectively. Compound 20 which was generated in situ by heating phenacylthiocyanate(19)in acetic anhydride on treatment with hydrazine hydrate or phenyl hydrazine gives 21 and 22 respectively. Also 20 reacted with malononitrile or with ethyl cyanoacetate to give23and24,respectively.

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