Chemistry

Advances in Heterocyclic Chemistry, Vol. 50 by Alan R. Katritzky (Ed.)

By Alan R. Katritzky (Ed.)

(from preface)Volume 50 of Advances in Heterocyclic Chemistry contains 4 chapters. Howard D. Perlmutter has contributed a survey of 1,2- and 1,3-diazocines. this can be the fourth in a chain of stories by means of PerlmutterĀ» whose earlier surveys contain azocines (Volume 31,1982), 1,4-diazocines (Volume forty five, 1989), and 1,5-diazocines (Volume forty six, 1989). the current bankruptcy completes this therapy of 8-membered heterocycles containing nitrogen.R. E. Busby has written a bankruptcy on thiadiazines containing adjoining sulfur and nitrogen ring atoms. This bankruptcy enhances one in quantity forty four which handled sulfamides of this sort. H. Quiniou and O. Guilloton of Nantes have coated the chemistry of monocyclic 1,3-thiazines, a bunch that, strangely, has now not been reviewed comprehensively for a few years. ultimately, E. V. Kuznetsov and that i. V. Shcherbakova of Rostov collaborate with A. T. Balaban of Bucharest in a precis of the chemistry of benzo[c]pyrylium salts. This assessment enhances the evaluation via a bunch of authors below the management of Balaban who lined the chemistry of pyrylium salts in complement 2 of this sequence, which seemed in 1982.

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If cyanogen bromide was used instead of orthoesters, triazocines 235 (R2 = NH2) resulted. Reduction of 234 ( R = R' = Me), followed by condensation with diethyl carbonate, gave urea 234 (R = R' = Me, X = 0). A similar reaction starting with 234 54 HOWARD D. PERLMUTTER [Sec. B (R = H, R' = OMe) and using carbonyl and thiocarbonyldiimidazoles yielded urea 236 (R = H, R' = OMe, X = 0) and thiourea 236 (R = H, R' = OMe, X = S), respectively. Condensation of the latter compound with methyl iodide in the presence of sodium methoxide afforded 235 (R = H, R' = OMe, R2 = SMe) (83T479, 83T1199).

Ulrich and co-workers found that Lossen rearrangement of the 0-mesylate of 112 in base gave 104 in yields better than these found in previous syntheses (78JOC1544). Schmidt reaction of tetralone 114 gave, in addition to the expected isomeric benzazepinones, an unusual product of further ring expansion: the eight-membered cyclic urea 115 (86JHC975). Cartier and co-workers treated the E-homovincamone derivative 116 with thionyl chloride to isolate 117 and 118 as major and minor products, respectively (76BSF1962).

Diazotization of 226, followed by cyclization, afforded tetrazocines (see Section V,B, 1 ,a). In a similar reaction, treatment of diamine 228 with N,N'-carbonyldiimidazole afforded compound 229 (82MI3). Finally, when 230 was reacted with polyphosphoric acid, cyclized product 231 was isolated (8OIZV 1886). Sec. A] 53 DIAZOCINES, TRIAZOCINES. TETRAZOCINES 'R ' 227 226 q 228 CONH 229 230 4. I ,3,6-Triazocines The initial report of the reaction of an imidazoline with thionyl chloride to give a triazocine was found to be in error, the correct structure being an imidazolidone (56JA6144).

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