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 studies through Perlmutter» whose past 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 gaggle that, unusually, has no longer been reviewed comprehensively for a few years. eventually, 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 evaluation enhances the overview 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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Additional info for Advances in Heterocyclic Chemistry, Vol. 50
113 29 DIAZOCINES. TRIAZOCINES. TETRAZOCIN ES Sec. A] 114 115 116 117 118 Rose-Bengal sensitized photooxygenation of cyclic tryptophan derivative 119 gave 1,3-diazocine-2,6-dione 120 (76H53). Murato and coworkers reductively cleaved p-carboline derivative 121 and isolated the novel diazocinoindole 122 (77CPB 1559). 119 120 NHCOCOt . Bu H H H 121 122 30 [Sec. A HOWARD D. PERLMUTTER Swenton and co-workers showed that uracyl-alkyne photoadducts 123 [R'= H, R2 = n-CsHI1 (82TL4207); R' = F, R2 = n-C3H7 (83JOC2337); R' = SiMe3, R2 = n-C3H7 (83JOC2337)l yield the corresponding diazo- cines 124 on treatment with trimethylsilyl chlondelhexamethyldisilazine followed by silica gel.
PERLMUTTER [Sec. A ureas 134 (X = S; R = H; R' = H, Me; R2 = H, Me, Ph), while the same reaction using 3-(o-aminophenyl)propylureas gave 134 [X = S, R = R' = H, R2 = CONHAlk(Ar)] (86EGP235452). R' WR2 '4 H X 134 135 2 . Chemistry and Applications a. Eight-Membered Ring Preserved: Substitution at Nitrogen, Sulfur, and Carbon. Dihydroxyurea 126 evinced antibacterial activity (84USP4454133). Benzo-fused ureas and thioureas 134 (X = 0, S) were useful as potential herbicides (75MI7), while compounds 134 [X = S, R = R' = H, R2 = CONHAlk(Ar)] specifically were used as intermediates for bioactive compounds (86EGP235452).
C. Via Condensations. Krakowiak et al. condensed the sodium salts of N,N’-ditosyl and N,N’-dibenzenesulfonyl-l,5-diaminopentanes with an excess of dibromomethane to obtain diazocine 167 [R = H; R‘ = Ts (83MI3), Bs (84MI2)I. Using a triamine instead of a diamine yielded a triazocine (see Section IV,A). Imidazolium salts 182, described as models for tetrahydrofolate coenzymes, underwent carbon transfer to bifunctional nucleophiles such as I ,5-diaminopentane to yield amidinium salt 183. 3 1,3-Diazocines 184 (Ar = Ph, 4-ClCsH4, 2-BrC6H4; R’= H, Me, Ac; R2 = H, Me, OH; R3 = H, Me; R4 = H) were obtained by reacting iminoesters with diamines (Scheme 8) (75USP3926994).
Advances in Heterocyclic Chemistry, Vol. 50 by Alan R. Katritzky (Ed.)