By Alan R. Katritzky
Meant for natural chemists, this quantity follows the layout of earlier volumes and gives updated info on chosen components of heterocyclic chemistry.
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Extra info for Advances in Heterocyclic Chemistry, Vol. 39
AcOH 2. With Aluminum Hydrides The reduction of isoquinolinium salts in aprotic solvents with LAH leads to the formation of I ,2-dihydroisoquinolines (195), in which the enamine system can undergo subsequent reaction with electrophiles. lo2 LiAIH, 'R LiAIH, 'Me Ph Ph J. INDOLES Although indoles are not normally reduced under neutral conditions with LAH or NBH, tetra-n-butylammonium borohydnde has recently been apIo2S. F. Dyke, R. G. Kinsman, P. Warren, and A. W. C. White, Tetrahedron34,241 (1978).
29,71 (1981). E. E. Knaus and K. Redda, Can. J. Chem. 55, 1788 (1977). Sec. C] REDUCTION O F NITROGEN HETEROCYCLES 23 Sodium cyanoborohydride is a more selective reducing agent than boroh ~ d r i d eAn . ~ investigation ~ into the reduction of 4-substituted pyridinium salts (1 16) would seem to bear this out. With these the 4 substituent directs hydride attack to the a positions, and in protic solvents the tetrahydropyridines 117 are isolated. ~’ However, raising the temperature is known in one instance (4-carboxamido) to cause concomitant reduction of the ketone carbonyl group.
00% yield NaBH3CN * P h a P h P h a p h LiAIH, R MeHRM e + ' ' d , r y M e YaMe (24 I R = H , Me THF 40 h ';I 7' (224 OH I + Me'"' RE^ + M e A O H .. H NH, h e (24 (23 t 'e+CHMe I @4OAiH3 Il7 II8 119 V. Jager and V. Buss, Liebigs Ann. , 101 (1980). A. Alberola, A. M. Gonzalez, M. A. Laguna, and F. J. Pulido, Synthesis, 413 (1983). A. Cem, C. De Micheli, and R. Gandolfi, Synfhesis. 710 (1974). A. L. Khurana and A. M. Unrau, Can. J. Chem. 53,301 1 (1975). 40 [Sec. M JAMES G . KEAY L. 122 R = Me, R'=Me,CH,Ph LiAIH, MeLJGo2Me Me Me M.