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 crew of compounds often called meso-ionic heterocycles and incorporates a beneficial common definition of the time period. the second one bankruptcy (Litvinov and Gol'dfarb) offers with structures with (or extra) thiophene (or selenophene) jewelry without delay fused jointly. The 1,2,3-triazines, in addition to 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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104, 1550 (1971). E. Brunn, E. Funke, H. Gotthardt, and R. Huisgen, Chem. Ber. 104, 1562 (1971). 46 (a) K. Potts and U . P. Singh, Chem. , 66 (1969); (b) K. T. Potts and D. McKeough, J. Amer. Chem. Soc. 95, 2749 (1973); (c) K. T. Potts and J. Baum, J. Chem. ,Chem. , 833 (1973); (d) H. Matsukubo and H. , 412 (1974); J. Chem. ,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).
44, 826 (1971). R. Huisgen, E. Funke, F. C. Schaefer, H. Gotthardt, and E. , 1809 (1967). 63 K. T. Potts and D. N. Roy, Chem. , 1062 (1968). " A. [Sec. C W. D. OLLIS AND C. A. RAMSDEN 24 C. THIAZOLES 1. 65 A second route to meso-ionic 1,3-thiazol-5-ones(105) is provided by 1,3-dipolar cycloaddition. 44962 6 R' R2 -N,+ R' o- kS R2-N"COZH R3 (105) R' ks ] RZ- N p O E t BF4R3 1106) (107) The meso-ionic 1,3-thiazol-5-ones(105) show an interesting range of reactions. ~~ 2. "~ s4A. Lawson and C. E. Searle, J.
Shiba, H. Yoshida, and S. Fujimori, Chem. , 1591 (1970); (b) H. Kato, T. Shiba, and Y. Miki, J. Chem. , Chem. , 498 (1972). 9* M. Hashimoto and M. Ohta, Bull. Chem. Soc. Jap. 34, 668 (1961). =E. B. Roche and L. B. Kier, J. Pharm. Scl. 54, 1700 (1965). lWC. Ainsworth, Can. J. Chem. 43, 1607 (1965). lol D. J. McCaustland, W. H. Burton, and C. C. Cheng, J. Heterocycl. Chem. 8, 89 97 (1971). Sec. VILE1 MESO-IONIC COMPOUNDS 33 nones (146)are colorless, reasonably stable compounds, but they are clearly more reactive toward nucleophilic reagentslo2than the sydnones (1).
Advances in Heterocyclic Chemistry, Vol. 19 by A. R. & Boulton, A. J. [Eds]. Katritzky