Preparation of New Nitrogen-Bridged Heterocycles. 46. Selective Formation of 4(1H)-8,8a-Dihydro-1,4-thiazino[3,4,5-cd]indolizinone and (E)-3-(1,3-Oxathiol-2-ylidene)-2(3H)-indolizinone Derivatives.

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  • Preparation of New Nitrogen-Bridged Het

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The reactions of (Z)-3-[mercapto(methylthio)methylene]-2(3H)-indolizinones with bromoacetonitrile and bromoacetates in the presence of a base gave the corresponding 4(1H)-8, 8a-dihydro-1, 4-thiazino[3, 4, 5-cd]indolizinone derivatives, but similar treatment of the same compounds with some phenacyl bromides provided a quite different type of product, (E)-3-(5-aryl-1, 3-oxathiol-2-ylidene)-2(3H)-indolizinones, in 12-74% yield with the evolution of methanethiol. Interestingly, the reactions of (Z)-3-[mercapto(phenacylthio)methylene]-2(3H)-indolizinones and iodomethane in the presence of a base did not afford the expected (Z)-3-(5-aryl-1, 3-oxathiol-2-ylidene)-2(3H)-indolizinones, but gave only the same (E)-isomers in 22-53% yields. The stereochemistry about the C3-C2' double bond in these 3-(5-aryl-1, 3-oxathiol-2-ylidene)-2(3H)-indolizinones was determined to be (E) by X-ray analysis.

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