By A. R. & Boulton, A. J. [Eds]. Katritzky

The current quantity involves 4 chapters. the 1st (by Ollis and Ramsden) classifies and discusses the chemistry of that attention-grabbing team of compounds referred to as meso-ionic heterocycles and features a precious basic definition of the time period. the second one bankruptcy (Litvinov and Gol'dfarb) offers with platforms with (or extra) thiophene (or selenophene) jewelry at once fused jointly. The 1,2,3-triazines, besides the better-known 1,2,3-benzotri-azines and different fused 1,2,3-triazine structures, are mentioned within the 3rd bankruptcy, by way of Kobylecki and McKillop. within the final bankruptcy George, Khetan, and Gupta deal with heterocyclic syntheses which contain the addition of nucleo-philic reagents to acetylenic esters.

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4261 (1967). M. Ota (Takeda Chem. ), Japan 70 07,741 [CA 73, 14857d (1970)l. T. Potts, S. K. Roy, S. W. Schneller, and R. Huseby, J. Org. Chem. 33,2559 (1 968). IaG. Palazzo and L. Baiocchi, Gazz. Chim. Ifal. 96, 1020 (1966) [CA 66, 115652~ (1967)l. Sec. Gl 45 MESO-IONIC COMPOUNDS (212) (211) Nuclear magnetic resonance studies141on meso-ionic 1,2,4-triazol-3ones (200) were used to examine their relationship to the alternative 1,3,4-oxadiazol-2-imine structure (15 3). 142 Ph / Ph N / r N P h Ph-N/ll \N (213) (214) (215) The photolysis of the meso-ionic 1,4-diphenyl-1,2,4-triazo1-3-one RZ= H) was statedg7' to yield phenyl isocyanate (13%), N,N'-diphenylurea (23%), and the bicyclic compound 215 (49%).

Perkin Trans. Eicher and V. -D. Hekman, Angew. , Ed. Engl. 11, 926 (1972). 47 G. -P. Fleury, Bull. Soc. Chim. , 4636 (1968). 45 Sec. C,H,) as supporting the meso-ionic structure (77). 007%. They have also shown that azlactones 76 + 77 participate in 1,3-dipolar cycloaddition with a l k y n e ~ ~ ~ * ~ ~ and a l k e n e ~ In . ~ view ~ of the extensive earlier studies of azlactones (76), it is remarkable that their tautomerism with meso-ionic 1,3-oxazol-5ones (77) should have been recognized so recently.

W. Stele, W. K. Anderson, and W. F. Trager, Can. J. Chem. 50, 1026 (1972). 22 W. D. OLLIS A N D C. A. RAMSDEN [Sec. B Polycyclic meso-ionic 1,3-diazol-4-ones (93) are also known. These include Besthorn's Red (93a) which was first described in 1904. The discovery of Besthorn's Red and its subsequent formulation (93a) forms an interesting part of the history of meso-ionic c o m p o u n d ~ . ~ * ~ ~ Recently,58ban analogous meso-ionic 1,3-diazo1-4-one (93b) was unexpectedly encountered as the product of the reaction between 1azaphenothiazine and chloroacetic anhydride.

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