Synthesis of heterocyclic systems with a carbohydrate fragment |
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Authors: | A V Samet A N Yamskov B I Ugrak V V Semenov |
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Institution: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913 Moscow, Russian Federation |
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Abstract: | Levoglucosenone reacts with α-aminoazoles to yield azolo1,5-a]pyrimidine systems fused with a carbohydrate fragment. The reaction oocurs much more smoothly than in the case of other α,β-unsaturated
ketones. The reactions of levoglucosenone with β-dicarbonyl compounds (dimedone, barbituric acid) in the presence of a base
results in the pyran ring closure, which has never been observed earlier in reactions of β-dicarbonyl compounds with α,β-unsaturated
ketones under the conditions of basic catalysis. The structures of products were established by IR and NMR spectroscopy.
For Part 3, see Ref. 1.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 553–558, March, 1997. |
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Keywords: | levoglucosenone α -aminoazoles dimedone barbituric acid 2-aminopyridine ethyl β -aminocrotonate stereoselective heterocyclization |
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