Vinyl azides in heterocyclic synthesis. Part 6. Synthesis of isoquinolines by intramolecular aza-Wittig reaction
- 1 January 1987
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 4,p. 921-926
- https://doi.org/10.1039/p19870000921
Abstract
Azidocinnamates containing ortho-carbonyl substituents are versatile intermediates for heterocyclic synthesis. Isoquinolines (8) and (9) are formed under mild neutral conditions by intramolecular aza-Wittig reactions of iminophosphoranes, readily derived from azides (1) and (2), respectively, with triethyl phosphite. The azafluoranthene (10) can also be prepared from the azide (3)via the isolable iminophosphoranes (11) and (12). Thermolysis of the azides (1) in toluene or xylene gives the 4-substituted indoles (13) in varying yield (Table 2). Similarly the indoles (14) and (19) are formed from the azides (3) and (6a and b) respectively.This publication has 2 references indexed in Scilit:
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- Synthese eines aus Othonna cylindrica DC isolierten MethylsalicylsäurederivatsEuropean Journal of Inorganic Chemistry, 1976