ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

1,3-Dipolar cycloadditions of heterocycles.16. Reduction of isoxazolines - a pathway to condensed oxazines

Ľ. Fišera, A. Závacká, and L. Štibrányi

Department of Organic Chemistry, Slovak Technical University, CS-812 37 Bratislava

Abstract: 1,3-Dipolar cycloaddition of acetonitrile oxide at substituted 1,3-dioxep-5-enes produces a diastereomeric pair of endo and exo adducts. A prepara­tion of n + 1-memhered heterocycles from л-membered ones via a simple sequence of 1,3-dipolar cycloaddition, reduction, and cyclization is de­scribed. Reduction of isoxazolines with lithium-aluminium hydride fur­nishes a mixture of heterocyclic erythro and threo /-amino alcohols VI, VII, IX, X which upon cyclization with 4-nitrobenzaldehyde produce condensed tetrahydro-l,3-oxazine derivatives XI, XII.

Full paper in Portable Document Format: 415a609.pdf

Chemical Papers 41 (5) 609–622 (1987)