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

By Alan R. Katritzky

Meant for natural chemists, this quantity follows the layout of past volumes and offers up to date info on chosen parts of heterocyclic chemistry.

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Robert, Bull. Chirn. , 2859 (1 972). 48 JAMES G . KEAY [Sec. F agent leads to a time-dependent mixture of products (282 - 284). Other substituted and dipyridazinones146yield hexahydropyridazines with LAH. R3 Do I R’ (281) LIAIH, * Rh + \N . R3Q HN, I I I RQN--N R’ R’ R’ (284 (4 (284) R’= H,Me,Ph; RJ= Me,Ph F. 147The ratio of these products varies markedly, depending on the presence of sodium hydroxide. 147The presence of sodium hydroxide retards formation of trimethyl borate, and a large increase in the proportion of 286 and 287 is now observed.

3, 89 (1975). 56 JAMES G. KEAY [Sec. B V. Reductions of Heterocycles Containing Three Nitrogen Atoms A. 1,2,3-TRIAZOLES 1,2,3-Triazolium salts (335) are not readily reduced by NBH. 17sThis reactivity pattern is explained by the need for an immonium ion for successful reaction. The presence of a C-2 substituent in 336 makes this possible; the lack ofsuch a substituent localizes the double bond joining C-4 and C-5. :$t NaBH, Ph Me’ e... Me’ Me - I R = H,Ph \Q M e - Ph . q L - I Ph (336) ($4 B. 1,2,4-TRIAZOLES 1,2,4-Triazoliumsalts (338)are readily reduced to the dihydro derivatives 339, (triazolines) by aqueous NBH.

C. Roze, and G . Duguay, J. Chem. , 72 (1982). KEAY [Sec. A in such systems. Iz7This the imine bond in 2-phenyl-6H-l,3-thiazines results partially from the bond polarization effects of the phenyl group and partially from protonation. More powerful reducing agents affordring cleavage. lZ8The isolation of the benzothiazole 245 as a minor product points to C-2-S rupture prior to reduction of the imine. DcoR NaBH,CN Ph H,O' * HDcoR Ph (241) (242) IV. Reductions of Heterocycles Containing Two Nitrogen Atoms A.

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