POLYFUNCTIONALIZED HEXAHYDRO-1(2H)-PENTALENONES BY REARRANGEMENT OF BICYCLIC 1,2-OXAZINE N-OXIDE DERIVATIVES

DOI: 10.1016/S0040-4020(01)83495-5

Source and publish data:

Tetrahedron p. 2441 - 2449 (1984)

Update date:2022-07-30

Topics:

Authors:

Barbarella, G.

Brueckner, S.

Pitacco, G.

Valentin, E.

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Article abstract of DOI:10.1016/S0040-4020(01)83495-5

The title heterocycles rearrange into a mixture of diastereomeric hexahydro-1(H)-pentalenone derivatives, which undergo nucleophilic eliminative ring fission by methanol to give 1-amino-2-nitroalkylated cyclopentancarboxylic esters.The X-ray structure determination of hexahydro-2-methyl-2-nitro-3-phenyl-6a-(1-piperidinyl)-1(2H)-pentalenone <2S-(2α,3α,3aα,6aα)> is also reported.

Full text of DOI:10.1016/S0040-4020(01)83495-5

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