Intramolecular 1,3-dipolar cycloaddition at the periphery of heterocyclic systems. Part 1. Facile oxime–nitrone isomerisation at the periphery of pyran and 1-benzopyran
- 1 January 1995
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 14,p. 1857-1862
- https://doi.org/10.1039/p19950001857
Abstract
4-(Alk-2-enylamino)-2-oxo-2H-1-benzopyran-3-carbaldehyde oximes 5 underwent thermally induced 1,3-dipolar cycloaddition under mild conditions giving isoxazolo[3,4-d][1]benzopyrano[4,3-b]pyridine derivatives 6 in good yields. The features of the oxime–nitrone isomerisation and nitrone–olefin cycloaddition are discussed.Keywords
This publication has 26 references indexed in Scilit:
- Stereospecific synthesis of functionalized cyclopentanesTetrahedron Letters, 1989
- Formation of functionalized cyclic ethers by intramolecular nitrile oxide cycloadditionsTetrahedron Letters, 1988
- Intramolecular oxime olefin cycloadditions. Stereospecific formation of functionalized pyrrolidines.Tetrahedron Letters, 1988
- Fused β-lactams via intramolecular dipolar cycloadditionTetrahedron Letters, 1987
- Prototropic routes to 1,3- and 1,5-dipoles, and 1,2-ylides: applications to the synthesis of heterocyclic compoundsChemical Society Reviews, 1987
- Novel transformations leading to 3-benzylindolizidin-2-onesThe Journal of Organic Chemistry, 1987
- XY–ZH systems as potential 1,3-dipoles. Part 1. Background and scopeJournal of the Chemical Society, Perkin Transactions 1, 1984
- XY–ZH systems as potential 1,3-dipoles. Part 3. Isoxazolidines from the 1:1 cycloaddition of oximes with dipolarophilesJournal of the Chemical Society, Perkin Transactions 1, 1984
- XY–ZH systems as potential 1,3-dipoles. Part 2. Oxime cycloadditions: formation of 2 : 1 adductsJournal of the Chemical Society, Perkin Transactions 1, 1984
- Aufbau neuer heterocyclen mittels intramolekularer nitron-olefin-cycloadditionenTetrahedron Letters, 1970