Synthesis of 2-Methylpyrrolo[1,2-a]pyrazin-1(2h)-one

Abstract

The synthesis of 2-methylpyrrolo[l,2-alpyrazin-l(2H)-one (2) present in the insect feeding deterrent peramine (1) through oxidation of the saturated lactam (3) is described. The preparation of the related 6-methyl-1 H-pyrrolo[2,3-clpyridin-7(6 H)-one (12) through a Lewis-acid-catalysed cyclization of the amide acetal (7) is also described.

A Novel Synthesis of Arylpyrrolo[1,2-a]pyrazinone Derivatives

“…Brimble et al have reported the synthesis of 2-methyl-1-pyrrolo[1,2-a] pyrazinone (5) from methyl pyrrole-2-carboxylate (4) and 1,2-dibromoethane (Scheme 1) [2]. Based on this scheme, we wished to prepare compounds 2 by replacing the 1,2-dibromoethane with 1,2-dibromo-1-phenylethane, but the N-alkylation of compound 4 failed to take place and 2-bromo-1-phenylethene was separated from the reaction mixture.…”

Synthesis and pharmacological evaluation of 1,2,3,4-tetrahydropyrazino[1,2-a]indole and 2-[(phenylmethylamino)methyl]-1H-indole analogues as novel melatoninergic ligands

“…A better yield of 5b (60%) could be achieved by using cobalt-(II)-chloride/sodium borohydride as reducing agent. 17 …”

A Review of the Synthetic Strategies toward Dihydropyrrolo[1,2-a]Pyrazinones

“…Probably the reaction starts with the substitution of the bromine by the amine, followed by lactamization. Several examples were reported [25,27,80]. In the framework of agelastatin total synthesis, some examples were reported where, in the presence of sodium hydride, an amide substituted a bromine at the side chain connected to nitrogen, proving that the opposite order of reactions is also possible [81,82].…”