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 is often the fourth in a sequence of stories by way of Perlmutter» whose earlier surveys comprise 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 lined the chemistry of monocyclic 1,3-thiazines, a bunch that, strangely, 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 evaluation enhances the evaluation by means of a bunch 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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These compounds have diuretic properties (81USP4283334; 82USP4340734; 82USP4347248). Analogously prepared were 148 (R' = Ph, pCIC6H4; R2 = H); these compounds were evaluated for bacteriocidal and fungici- 36 HOWARD D. PERLMUTTER [Sec. A dal properties (82JICll70). These same properties were evaluated in thiazolidinones 149 (R = R’ = H) and their salts, which are prepared by condensing 105 with chloroacetic acid and ethyl chloroacetate, respectively. Also evaluated was sulfamidophenylazo derivative 149 [R = H, R’ = N2C6H4S02NH2(p)],2-arylidene derivatives (149) (RR’are =CHPh and =CHthienyl), and the products of bromine addition to the latter two compounds.

2 . Eight-Membered Ring Preserved: Other Reactions When spirodiazirinodiazocine 44 (see Section II,A,3,b) was heated in benzene containing triethylamine, cyclohexenyldiazocine 80 resulted (76JOC3229). There have been a number of reports of photochemical ( Z ) (40) and (E)- (12) isomerizations in 1,2-diaza-I -cyclooctenes (72TL4565; 76CB5 18; 81JOC303; 85CJC 1829). Eamples of reductions in 1,2-diazocines are reduction of 1,2-diaza-2,840 (56RTC1159; 59JA217; cyclooctadienes 28 to 1,2-diaza-l-cyclooctenes 76CB5 18) and to 1,2-diazacyclooctane 39 (56RTC1159);reduction of 40 to 39 (69JOC3237); and lactam-amine transformation (73BSF2029).

The latter compounds afforded pyridones 125 on mixing with potassium terr-butoxide. These findings were taken as strong evidence for the intermediacy of diazocines 124 in the base-catalyzed fragmentationof 123to give 125,a mechanism that was strongly suggested by 15N and I3C labeling and kinetics studies and ruled out a Dewar pyridone-type intermediate (82TL4207; 83JOC2337). fi R' 0 R' H 0 H 123 124 125 c. Via Condensations. Berke and Rosen reported the 1 : 1 reaction of glutaraldehyde and urea in alkaline solution afforded diazocine 126, although no structure proof was offered.

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