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Synthesis 2008(18): 2883-2890  
DOI: 10.1055/s-2008-1067243
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Concise Synthesis of Benzo[h]- and Pyrido[3,2-h]-δ-carbolin-2,4-diones from One-Pot Reaction of β-Lactam Carbenes with Naphthyl and Quinolyl Isonitriles

Gao-Feng Shi, Zhi-Mei Kang, Xiao-Ping Jiang, Ying Cheng*
Chemistry Department, Beijing Normal University, Beijing 100875, P. R. of China
Fax: +86(10)58805558; e-Mail: ycheng2@bnu.edu.cn;
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Publikationsverlauf

Received 28 May 2008
Publikationsdatum:
22. August 2008 (online)

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Abstract

The one-pot reaction of β-lactam carbenes with 1-naphthyl or 5-quinolyl isonitriles followed by treatment with aqueous hydrochloride produced benzo[h]-δ-carbolin-2,4-diones or pyrido[3,2-h]-δ-carbolin-2,4-diones, respectively, in moderate yields. The easy availability of β-lactam carbenes and aryl isonitriles, and the simple chemical manipulations render our approach practical in the synthesis of various novel aryl fused δ-carboline derivatives, which are not easily prepared by other synthetic methods.

Key words

carbenes - β-lactams - isonitriles - benzo[h]-δ-carbolin-2,4-dione - pyrido[3,2-h]-δ-carbolin-2,4-dione

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CCDC 686809 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.