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2005
Pyran derivatives
R 0340
Cross-Condensation of Derivatives of Cyanoacetic Acid and Carbonyl ComPart 2. One-Pot Synthesis of Substituted 2-Amino-7-methyl-5-oxo02- 128 pounds.
-4,5-dihydropyrano[4,3-b]pyrans in Ethanol and Ionic Liquid [bmim][PF6]. —
Three-component condensation of hydroxypyranone (I) with cyanoacetic acid derivatives and aldehydes (III) in EtOH or [bmim]PF6 provides efficient access to substituted
dihydropyrano[4,3-b]pyrans (IV) (13 examples). Use of isatin instead of aldehydes
affords spiropyranopyrans (VIII). The yields in the ionic liquid are ca. 10-14% higher
than that in EtOH. Attempts to conduct the three-component condensation of pyranone
(I) with malononitrile (IIb) and piperidinone (VIII) fail and furnish spiroheterocycle
(IX). Evidently, pyranone (I) is not involved in this reaction. — (SHESTOPALOV*,
A. M.; ZLOTIN, S. G.; SHESTOPALOV, A. A.; MORTIKOV, V. Y.;
RODINOVSKAYA, L. A.; Russ. Chem. Bull. 53 (2004) 3, 573-579; Zelinsky Inst.
Org. Chem., Russ. Acad. Sci., Moscow 117913, Russia; Eng.) — R. Staver
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