Synlett 2010(15): 2285-2288  
DOI: 10.1055/s-0030-1258030
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Tetrahydropyrrolo[1,2-a]quinoxalines and Tetrahydro­pyrido[1,2-a]quinoxalines via a One-Pot CuI-Catalyzed Aryl Amination-Hydrolysis-Condensation Process

Lanting Xua, Yongwen Jiangb, Dawei Ma*b
a Department of Chemistry, Fudan University, Shanghai 200433, P. R. of China
b State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. of China
Fax: +86(21)64166128; e-Mail: madw@mail.sioc.ac.cn;
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Publication History

Received 27 May 2010
Publication Date:
19 August 2010 (eFirst)

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Abstract

CuI-catalyzed coupling of 2-halotrifluoroacetanilides with l-proline or pipecolinic acid in DMSO at 90-110 ˚C followed by in situ hydrolysis at 100 ˚C afforded tetrahydropyrrolo[1,2-a]quinoxalines or tetrahydropyrido[1,2-a]quinoxalines.

Key words

catalysis - coupling - heterocycle - quinoxaline - one-pot process