1,2,4-TRIAZINES IN ORGANIC SYNTHESIS. 9. SYNTHESIS OF 3-(3-ETHYLINDOL-2-YL)-5,6,7,8-TETRAHYDROISOQUINOLINE USING THE FISCHER REACTION UNDER THE USUAL CONDITIONS AND WITH MICROWAVE IRRADIATION

Abstract

The nucleophilic substitution of hydrogen in 3-methylthio-1,2,4-triazine by the carbanions of nitrobutane and 4-nitrobut-1-ene gave oximes, the selective fission of which using sodium dithionite gave ketones in the case of compounds with a saturated carbon chain. Ketones in Diels-Alder reaction with 1-pyrrolidinocyclohex-1-ene gave 3-acyl-1-methylthio-5,6,7,8-tetrahydroisoquinolines. Phenylhydrazones of the compounds obtained underwent Fischer reaction under usual conditions and also when using microwave irradiation on a solid support. The final 3-(3-ethylindol-2-yl)-5,6,7,8-tetrahydroisoquinoline was obtained via reductive desulfuration using Raney nickel in ethanol.

How to Cite
Lipin'ska, T. Chem. Heterocycl. Compd. 2001, 37, 231. [Khim. Geterotsikl. Soedin. 2001, 256.]

For this article in the English edition, see DOI https://doi.org/10.1023/A:1017575718196