Stereochemistry of electrophilic annelation of 2-allyl- (and 2-cyclohexen-1-yl)thio-1,5-naphthyridines to thiazolo]3,2-a]-1,5-naphthyridinium salts |
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| Authors: | A. M. Shestopalov V. N. Nesterov Yu. A. Sharanin V. P. Litvinov V. Yu. Mortikov V. E. Shklover Yu. T. Struchkov |
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| Affiliation: | (1) T. G. Shevchenko Voroshilovgrad State Pedagogical Institute, 348011 Voroshilovgrad;(2) N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, 117913 Moscow;(3) A. N. Nesmeyanov Institute of Heteroorganic Compounds, Academy of Sciences of the USSR, 117813 Moscow |
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| Abstract: | Methods have been developed for the synthesis of 3-cyano-5,8-ethano-5,6,7,8-tetrahydro-1,5-naphthyridine-2(1H)-thione and 2-allyl- (and 2-cyclohexen-1-yl)thio-1,5-naphthyridines, and their structures have been studied. X-ray diffraction examination has shown that these compounds contain a disordered contact between the free electron pair of the pyridine nitrogen and the  -bond of the allyl grouping, so that they react stereoselectively with halogens to give thiazolo[3,2-a]-1,5-naphthyridinium salts.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 557–563, April, 1989. |
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