Substituted hydrazonals as building blocks in heterocyclic synthesis: a new route to arylhydrazonocinnolines

Authors: Al-Shiekh, Mariam A.; Medrassi, Hanady Y.; Elnagdi, Mohamed H.; Hafez, Ebtisam A.

Source: Journal of Chemical Research, Volume 2007, Number 7, July 2007 , pp. 432-436(5)

Publisher: Science Reviews 2000 Ltd

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Abstract:

2-heteroylhydrazonopropanals 2a-e and 3-oxo-2-arylhydrazonopropanals 2f-k were prepared via coupling of enaminones 1 with aromatic diazonium salts. Compounds 2a-c condensed with hydrazine hydrate to yield the corresponding hydrazones 3a-c which afford on cyclisation the cinnoline derivatives 6a-c, while condensation of 2g, j with hydrazine hydrate directly yielded the pyrazole derivatives 4g-j. Condensation of 2a-c, f, g with phenyl hydrazine gave the corresponding phenyl hydrazone derivatives 7a-c, f, g. Structures of 2a, h and 3a were assessed by single crystal X-ray analyses.

Keywords: 2-ARYLHYDRAZONOPROPANALS, ENAMINONES, ARYLHYDRAZON

Document Type: Research article

DOI: http://dx.doi.org/10.3184/030823407X234617

Publication date: 2007-07-01

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The Journal of Chemical Research is a monthly journal which has a broad international authorship and publishes research papers and reviews in all branches of experimental chemistry.
Recent papers have described new synthetic methods, new heterocyclic compounds, new natural products, and the inorganic chemistry of metal complexes. Now in its 34th year, the Journal of Chemical Research was established in 1977 as a joint venture by the British, French and German chemical societies and maintains the high standards set by the founding societies. Each paper is independently peer reviewed and only carefully evaluated contributions are accepted.
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