Journal
TETRAHEDRON
Volume 58, Issue 3, Pages 531-544Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(01)01153-X
Keywords
hetero Diels-Alder reaction; cycloaddition diastereoselectivity; selectivity; 1-oxa-1,3-buta-dienes; X-ray diffraction analysis
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Several different heterocyclic aldehydes, derived from pyrazole. pyrimidine, pyridine, indole and thiazole, were converted to polyheterocyclic compounds containing four to seven rings. The key steps in the sequence were a Knoevenagel condensation of the aldehyde and a heterocyclic carbonyl compound, such as pyrazolone and isoxazolone, followed by an intramolecular hetero Diets-Alder reaction. Most final products were isolated with high yield and diastereoselecivity. The isoxazolo fused cycloadducts formed interesting spiro-adducts upon heating. The cis nature of the bridging hydrogens of the heterocycles was evidenced by X-ray diffraction analysis.(dagger) (C) 2002 Elsevier Science Ltd. All rights reserved.
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