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Note | Regular issue | Vol 55, No. 5, 2001, pp.973-980
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9186
■ Synthesis of 4-(1-Dialkylaminoalkyl)pyrrolo[1,2-a]quinoxalines

Kazuhiro Kobayashi,* Takashi Matsumoto, Susumu Irisawa, Keiichi Yoneda, Osamu Morikawa, and Hisatoshi Konishi

*Department of Materials Science, Faculty of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan

Abstract

The reaction of 1-(2-isocyanophenyl)pyrroles (1), which were readily prepared from commercially available or known 1-(2-aminophenyl)pyrroles by formylation in refluxing ethyl formate followed by dehydration with POCl3/Et3N in THF, with Eschenmoser's salt (2) proceeded smoothly at room temperature to give the dimethyl(pyrrolo[1,2-a]quinoxalin-4-ylmethyl)ammonium iodides (3) in good yields (74—75%). 1-(2-isocyanophenyl)pyrrole (1a) was also found to react with a range of iminium salts (5) and (7), derived from secondary amines and aldehydes in the presence of Me3SiCl/NaI/Et3N, to give 4-(1-dialkylaminoalkyl)pyrrolo[1,2-a]quinoxaline derivatives (6), (8), and (9) in isolated yields ranging from 47 to 99%.