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

Organic

By Alan R. Katritzky

ISBN-10: 0120206390

ISBN-13: 9780120206391

Meant for natural chemists, this quantity follows the structure of earlier volumes and gives up to date details on chosen components of heterocyclic chemistry.

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Extra resources for Advances in Heterocyclic Chemistry, Vol. 39

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1 the 1 position and subsequent reduction of the enamine system is determined by the nature and position of ring substituents. Generally, tetrahydro adducts are formed. '''Jol The benzyl group must contain a nitro group in order to weaken the ring-substituent D bond. M Me e m ' M e NaBH4 M Me e 3 +' Me M Me e S N 0 2 Me Reaction of the isoquinolinium salt 191 with NBH gave the 1,2-dihydroisoquinoline 192 in high yield. ' J. L. Neumeyer, M. McCarthy, K. K. Winhardt, and P. L. Levins, J. Org. Chem.

Chem. Commun. 282 (1982). P. Aeberli, G. Cooke, W. J. Houlihan, and W. G. Salmond, J. Org. Chem. 40,382 (1975). 46 JAMES G . KEAY [Sec. E C. '@ a$R QJPR LiAIH, - THF * I I Me Me (27') (272) D. 1,2,4-OXADIAZOLES A variety of ureas and oximes can result from the reduction of lY2,4-oxadiazoles with LAH. The nature and position of substituents will determine the position of the attack and hence, the product. 141 LIAIH, Ph NHMe w H,CO N YdfP; k73) H,O' 'OH (2741 E. l~~ Sodium borohydride reduced the 1methylpyridazinium salts in water to the corresponding lY6-dihydropyridazine 276 in 40-60% yield.

A. A. Golubeva, A. V. Dovgilevich, and A. N. Kost, Khim. Geterotsikl. Soedin. 9, 1239 (1980). G. A. Golubeva, L. A. Sviridova, N. Y. Lebedenko, and A. N. Kost, Khim. Geterotsikl. Soedin. 4, 541 (1973). E. F. Godefroi, J. Org. Chem. 33, 860 (1968). REDUCTION OF NITROGEN HETEROCYCLES Sec. @ (26’) Treatment of the long-chain imidazolium salts 263 with potassium, sodium, and tetra-n-butylammonium borohydrides affords the acyclic diamines 264 and 265. 136Sodium cyanoborohydride failed to reduce the same salt under a variety of conditions.

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