Attempts to prepare some 3-substituted azolo[1,2-x]azines, intermediates in the synthesis of azaaplysinopsin derivatives

Some 3-substituted pyrrolo[1,2-a]azines 4a-d were prepared in low yields fr om the corresponding 2-methylpyridines 1a,b and pyrazine derivatives 1c,d b y quaternization with methyl bromoacetate followed by treatment with N,N-di methylformamide dimethyl acetal. Ethyl 2-pyridinylacetate (5) and 2-pyridin ylacetonitrile (6) were converted with 4-(2-bromo-1-dimethylaminoethylidene )-2-phenyl-5(4H)-oxazolone (9) into pyrrolo[1,2-a]pyridine derivatives 10 a nd 12, intermediates in the synthesis of azaaplysinopsins.