Reduction of quinolines to 1,2,3,4-tetrahydro derivatives employing a combination of NaCNBH3 and BF3·OEt2

Srikrishna, Adusumilli ; Jagadeeswar Reddy, T. ; Viswajanani, Ranganathan (1996) Reduction of quinolines to 1,2,3,4-tetrahydro derivatives employing a combination of NaCNBH3 and BF3·OEt2 Tetrahedron, 52 (5). pp. 1631-1636. ISSN 0040-4020

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/004040...

Related URL: http://dx.doi.org/10.1016/0040-4020(95)00991-4

Abstract

A regiospecific reduction of quinolines (and 1,10-phenanthroline) into the corresponding 1,2,3,4-tetrahydro derivatives using a combination of sodium cyanoborohydride and boron trifluoride etherate in refluxing methanol is described. Under the same conditions indole and acridine reduced to the corresponding dihydroderivatives, whereas acyl group transfer from oxygen to nitrogen atom is also noticed in the case of 8-acyloxyquinolines.

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