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

By Alan R. Katritzky

Tested in 1960, Advances in Heterocyclic Chemistry is the definitive serial within the area--one of serious value to natural chemists, polymer chemists, and lots of organic scientists. Written through proven gurus within the box, the excellent stories mix descriptive chemistry and mechanistic perception and yield an realizing of the way the chemistry drives the houses.

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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. '~~ aye ggMe _NaBH,, R=MeDMF N 95%EtOH NaBH, Me05% (334) R (332) ci *eMJf ( H R (333) R = M e , Aryl F.

Chem. 31, 3143 (1972). I. R. Gelling, W. J. Irwin, and D. G. Wibberley, J. C. S. Chern. , 1 1 38 (1969). W. J. Irwin, J. C. S. Perkin I, 353 (1972). 162 S. C. Pakrashi and A. K. Chakravarty, Indian J. Chem. 11, 122 (1973). S. C. Pakrashi and A. K. Chakravarty, J. C. S. Chem. , 1443 (1969). N. Finch, and H. W. Gschwend, J. Org. Chem. 36, 1463 (1971). 159 I6O Sec. J] REDUCTION OF NITROGEN HETEROCYCLES 53 Monosubstituted 4-quinazolines, with the exception of the 1and 3 - p h e n ~ l derivatives, '~~ do not undergo this ring opening reaction.

Tizane, Bull. Soc. Chim. , 3866 (1968). J. Elguero, R. Jacquier, and D. Tizane, Bull. Chim. , 1129 (1970). Sec. 132 (4 @54 @51) P h A M Me e 2. H,O + R' R ~ N + 1 (24 Reductant -C H,C H,OC H,C H,- Ph Me -C H,C H,OC H,CH,Me 132 I Ph (=. Product (96) LiAIH, 251 (SO), 252 (15) LiAIH, 251 (95) LiAIH, 251 (95) NaBH, 53 (60),254(40) NaBH, 5 3 (go), 254(10) J. Elguero, R. Jacquier, and S. Mignonac-Mondon, Bull. Chirn. , 2807 (1972). 44 JAMES G. KEAY [Sec. 133LAH Reduction of 255 in acetic anhydride has the overall effect of a reductive alkylation to give l-acetyl-2-ethyl-3,5,5-trimethylpyrazolidine (256).

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