The synthesis of 9-substituted N-benzyl-8-azabicyclo[4.3.0]non-4-en-7-ones by the intramolecular Diels–Alder reaction
- 1 January 1983
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 2,p. 387-394
- https://doi.org/10.1039/p19830000387
Abstract
The intramolecular thermal cyclisation of N-allyl-N-benzylpenta-2(E), 4-dienamide in refluxing NN-dimethylformamide gives N-benzyl-cis- and trans-8-azabicyclo[4.3.0]non-4-en-7-one; N-allyl-N-benzylhexa-2(E), 4(E)-dienamide gives (1RS, 3RS, 6SR)-3-methyl- and (1RS, 3RS, 6RS)-3-methyl-N-benzyl-8-azabicyclo[4.3.0]non-4-en-7-one. 9-Benzyl- and 9-isobutyl-N-benzyl-8-azabicyclo[4.3.0]-non-4-en-7-one are prepared by the analogous intramolecular thermal cyclisation of the appropriate α-substituted N-allylpenta-2 (E), 4-dienamides. The major products all have cis-fused rings, but all the possible configurations are formed in each case, including the products with trans-fused rings. The relative stereochemistries of the bicyclic products are assigned on the basis of their high-resolution 1H n.m.r. spectra.This publication has 6 references indexed in Scilit:
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