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

Photochemistry of heterocycles.16. Preparation and photochemistry of derivatives of 3a,4,6,6a-tetrahydropyrrolo[3,4-d]isoxazole

Ľ. Fišera, M. Konopíková, and Hj. Timpe

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

Abstract: Preparation and photochemistry of isoxazolines fused pyrrolidine deriva­ tives is described. The title compounds were prepared by 1,3-dipolar cycloaddition of the substituted benzenenitrile oxides on jV-phenyl-3-pyrroline. N-benzyl-3-pyrroline, and 7V-phenyl-2,5-dioxo-3-pyrroline. Whe­ reas structures with the pyrrolidine ring were photolabile, those having maleinimide moiety underwent methanolysis when irradiated in methanol, followed by the photolysis of the primary products to enamino aldehydes. The methanolysis was studied, its outcome was found to depend on reaction conditions. Reduction of the maleinimide derivative with NaBH₄ proceeded selectively.

Full paper in Portable Document Format: 411a95.pdf

Chemical Papers 41 (1) 95–105 (1987)