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Synthesis 2011(11): 1711-1716  
DOI: 10.1055/s-0030-1260044
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

One-Pot Synthesis of 9H-Indolo[3,2-c]pyrazolo[1,5-a]quinolines, 1H-Dipyrazolo[1,5-a:4′,3′-c]quinolines and 1H-Imidazo[4,5-c]pyrazolo[1,5-a]quinolines: Three New Heterocyclic Systems

Yiming Zhang, Ren Wang, Zongjun Shi, Wei Zhang*
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
Fax: +86(931)8625657; e-Mail: zhangwei6275@lzu.edu.cn;
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Received 14 February 2011
Publikationsdatum:
16. Mai 2011 (online)

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Abstract

An efficient synthesis of three new kinds of heterocyclic systems, 9H-indolo[3,2-c]pyrazolo[1,5-a]quinolines, 1H-dipyrazolo[1,5-a:4′,3′-c]quinolines and 1H-imidazo[4,5-c]pyrazolo[1,5-a]quinolines, has been achieved by the photochemical oxidative dehydrogenation and subsequent photocyclization and dehydrochlorination of 5-(2-chloro-1H-indol-3-yl)-, 5-(5-chloro-1H-pyrazol-4-yl)- and 5-(5-chloro-1H-imidazol-4-yl)-1-phenyl-4,5-dihydro-1H-pyrazoles in the presence of pyridine in acetone.

Key words

photodehydrogenation - photocyclization - 9H-indolo[3,2-c]pyrazolo[1,5-a]quinolines - 1H-dipyrazolo[1,5-a:4′,3′-c]quinolines - 1H-imidazo[4,5-c]pyrazolo[1,5-a]quinolines