Advances in Heterocyclic Chemistry, Vol. 39 by Alan R. Katritzky

By Alan R. Katritzky

Meant for natural chemists, this quantity follows the structure of past volumes and offers updated details on chosen components of heterocyclic chemistry.

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167 Sec. M] R 55 REDUCTION OF NITROGEN HETEROCYCLES a b C d e H 3-Me 5-Me 4,6 -di- Me 3,7-di -Me L. 1,4-DIAZEPINES Most of the work on the 1,4-diazepines has been directed toward the reduction of 0x0 derivatives and other functionalities. 1 7 1 ~ 1 7 2 M. Iy5-BENZODIAZEPINES 6,7-Benzo-1,2,4,5-tetrahydro-l,5-diazepines (333) may be obtained by the NBH reduction of the benzo-l,5-diazepinium chloride precursors 332. l~~ When the reduction was carried out in dimethylformamide, 2,4-dimethyl-1,5-dihydro-6,7-benzo-1,5-diazepine (334) was obtained.

Thompson, Aust. J. Chem. 17,877 (1964). 142 Y . Royer, M. Selim, and P. Rumpf, Bull. Soc. Chim. , 1060 (1973). C. Kaneko, T. Tsuchiya, and H. Igeta, Chem. Pharm. Bull. 22,2894 (1974). 47 REDUCTION OF NITROGEN HETEROCYCLES Sec. E] dropyridazines 277 were also isolated. The phenyl derivatives 276e,fwere the most stable, but all gradually decomposed when exposed to the atmosphere. The presence of a phenyl group favored the 1,6-dihydropyridazines 278 and in its absence the 1,4 isomers 279a p r e d ~ m i n a t e d .

A. ,2341 (1980). E. E. Knaus and K. Redda, J. vc1. Chem. 13, 1237 (1976). 22 JAMES G . KEAY (Sec. 82Products of this type have shown analgesic and antiinflammatory activity. NaBH, 0 I -N 'R * EtOH I HN\R ('12) The in situ preparation of N-sulfonylpyridinium salts and their concomitant reduction in the presence ofNBH has been studied. Using both sulfonyl chlorides and sulfonic acid anhydrides, Knaus and Redda obtained mixtures of both the 1,2- (114) and 1,4-dihydropyridines(115). 83 a2 83 Y. Tamura and M.

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