By Alan R. Katritzky (Ed.)
(from preface)Volume 50 of Advances in Heterocyclic Chemistry includes 4 chapters. Howard D. Perlmutter has contributed a survey of 1,2- and 1,3-diazocines. this is often the fourth in a sequence of reports by way of Perlmutter» 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 remedy 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, unusually, has no longer 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 evaluate enhances the evaluation by way of a gaggle of authors below the management of Balaban who coated the chemistry of pyrylium salts in complement 2 of this sequence, which seemed in 1982.
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Additional info for Advances in Heterocyclic Chemistry, Vol. 50
N-Oxalylbenzoate 204 (R = H, CI) was amidated with methylhydrazine and the product cyclized with sodium hydroxide in dimethylformamide (DMF) to give triazocinedione 205 (R = H, CI) (78JHC1309). , on the basis of X-ray diffraction analysis, suggested that the compound previously reported by Derieg et al. The same reaction was reported by Meguro and Kuwada (73CPB2375) [for an annelation reaction of 207 (R = R' = H), see Section IV,B,I]. BI Ph P h' H Br SCHEME I1 Sec. AJ DIAZOCINES, TRIAZOCINES. TETRAZOCINES 49 acozMg pcococl R Ph R 204 205 206 207 Condensation of piperonal derivative 208 with arylhydrazines afforded I ,4,5-benzotriazocines 209 (83M 123 1 ).
1,3,5-Triazocines Chapman found that nitration of bistrimethylenedinitramine 217 (R = CH2-morpholinyl)with a mixture of nitric acid, acetic anhydride, and ammmonium nitrate afforded 1,3,5-triazocine 218 (R = NO*) along with 4-nitromorpholine (49JCS163I ) . In a related reaction, Mannich condensation of 217 (R = H)with formaldehyde in the presence of primary amines yielded 218 [R = Me (49JCS1638), var. Use 218 219 220 214 216 21 5 SCHEME 12 52 [Sec. A HOWARD D. PERLMUTTER of ammonia instead of primary amines resulted in formation of 219 ( n = 1) [66JCS(C)870].
5-diazocine 187 [336764; 89AHC(46)I]. When the methylenebis(quin0- * NHNH? Me NeN02 -CH-Ph HCI * 188 Me -0 \CHPh NHNrCHPh PhCHO / PhCHO ___) cow H2S0, SCHEME 9 186 44 [Sec. B HOWARD D. PERLMUTTER CI 1 189 line) derivative (189) was heated with paraformaldehyde, diquinolinodiazocine 190 was obtained (78JHC649). 2 . Theory and Structure Huckel MO calculations on 1,3-diazocine (191) showed a resonance energy (RE) roughly equal to other alternant systems such as azocine (82AHC115), 1 ,Cdiazocine [89AHC(45)185], and 1,5-diazocine [89AHC(46)I].