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Communication | Regular issue | Vol 3, No. 11, 1975, pp.927-930
Published online, 1st January, 1970
DOI: 10.3987/R-1975-11-0927
Reaction of Diketene with Lactim Ethers

Tetsuzo Kato,* Yutaka Yamamoto, and Masatsugu Kondo

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


Reaction of 2-methoxy-1-pyrroline (Ia) with diketene without solvent affords 7-hydroxy-2,3-dihydro-1H,5H-indolizin-5-one (IIa) and 8a-methoxy-2-methylene-3,4,6,7,8,8a-hexahydro-2H-pyrrolo[2,1-b]-1,3-oxazin-4-one (IIIa) which, on treatment with sodium ethoxide, is transformed to 8a-methoxy-2-methyl-6,7,8,8a-tetrahydro-4H-pyrrolo[2,1-b]-1,3-oxazin-4-one (IVa).
Similarly, 2-methoxy-3,4,5,6-tetrahydropyridine (Ib) gives 2-hydroxy-6,7,8,9-tetrahydro-4H-quinalizin-4-one (IIb) and 9a-methoxy-2-methyl-7,8,9,9a-tetrahydro-4H,6H-pyrido[2,1-b]-1,3-oxazin-4-one (IVb).
Reaction of 2-methoxy-4,5,6,7-tetrahydro-3H-azepine (Ic) gives 10a-methoxy-2-methy1-6,7,8,9,10,10a-hexahydro-4H-azepino[2,1-b]-1,3-oxazin-4-one (IVc).