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Paper | Regular issue | Vol 31, No. 8, 1990, pp.1459-1471
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5386
The Reaction of 8-Methylpyrrolo[1,2-a]pyrazines with Dimethyl Acetylenedicarboxylate

Paul V. S. Kong Thoo Lin,* Robert Buchan, Martin Fraser, and Derek McHattie

*MRC, Labratory of Molecular Biology, Hills Road, Cambridge, CB2 2QH, U.K.

Abstract

2,8-Dimethylpyrrolo[1,2-a]pyrazine reacts with two molecular proportions of dimethyl acetylenedicarboxylate (DMAD) in toluene to give a reaction mixture from which five crystalline products were isolated. Four of the products were shown to be the isomeric tetracarbomethoxy 1:2 addcuts (9, 10, 14 and 15) and the fifth to be the tricarbomethoxydipyrrolopyrazine (7). A likely common reaction intermediate leading to the formation of all five products is suggested to be the 1:1 adduc (21). Reaction of 2,3,8-trimethylpyrroo[1,2-a]pyrazine with DMAD in toluene gave the corresponding compounds (17, 18, 19, 20 and 16).