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

ISBN-10: 0120206196

ISBN-13: 9780120206193

The current quantity comprises 4 chapters. the 1st (by Ollis and Ramsden) classifies and discusses the chemistry of that attention-grabbing team of compounds often called meso-ionic heterocycles and features a worthwhile basic definition of the time period. the second one bankruptcy (Litvinov and Gol'dfarb) bargains with structures with (or extra) thiophene (or selenophene) earrings without delay fused jointly. The 1,2,3-triazines, besides the better-known 1,2,3-benzotri-azines and different fused 1,2,3-triazine platforms, 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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P. 166. Israel Acad. Sci. Humanities, Jerusalem, 1971. 39 H. Gotthardt, R. Huisgen, and F. C. , 487 (1964). R. Huisgen, H. Gotthardt, H. 0. Bayer, and F. C. Schaefer, Chem. Ber. 103,261 1 (1970). 41H. Gotthardt and R. Huisgen, Chem. Ber. 103, 2625 (1970). Knorr, R. Huisgen, and G. K. Staudinger, Chem. Ber. 103, 2639 (1970). 41 R. Huisgen, E. Funke, H. -L. Panke, Chem. Ber. 104, 1532 (1 97 1). E. Funke, R. Huisgen, and F. C. Schaefer, Chem. Ber. 104, 1550 (1971). E. Brunn, E. Funke, H. Gotthardt, and R.

RAMSDEN 42 [Sec. G 3. 1269130 The most convenient method is by the treatment of 4-bromo-1,2,3-triazoliumsalts (197, X = Br) with sodium sulfide in dimethylformamide. Alternatively, Nmethylation of the isomeric 4- or 5-alkylmercapto-1,2,3-triazoles 198 or 199 with methyl tosylate gave intermediate triazolium salts (197, X = SR, Y = Tos), which yielded meso-ionic 1,2,3-triazole-4-thiones(196) by S-dealkylation by heating with piperidine. RZ R2 N-N / / -dpS-R’-N+@ R’ R3 R3 (196) (197) X)Y- R’ N=N R1-d,&SR2 (198) / N-N d’&SR2 (199) In contrast with the meso-ionic 1,2,3-triazol-4-ones (176) which are relatively stable to heat, the meso-ionic 1,2,3-triazole-4-thiones(196) rearrange when heated in benzene solution at 180”.

The meso-ionic 1,3,4-oxadiazole-2-thiones( 156) form methiodides (1 5 7)'lz which are easily hydrolyzed, yielding the acyclic esters (160a). The meso-ionic 1,3,4-oxadiazole-2-thione (156, R' = Me, R2 J. Sandstrom and I. Wennerbeck, Actu Chem. Scund. 20, 57 (1966). lloA. Ya. Lazaris, J. Org. Chem. USSR 3 , 1856 (1967) [CA 68, 1291Op (1968% A. Ya. Lazaris, J. Org. Chem. USSR 4, 1786 (1968) [CA 70, 19992s (1969)l. l12(a) R. Grashey, N. Keramaris, and M. , 5087 (1970); (b) A. Ya. Lazaris and A. N.

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Advances in Heterocyclic Chemistry, Vol. 19 by A. R. & Boulton, A. J. [Eds]. Katritzky


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