By A. R. & Boulton, A. J. [Eds]. Katritzky
The current quantity comprises 4 chapters. the 1st (by Ollis and Ramsden) classifies and discusses the chemistry of that fascinating crew of compounds referred to as meso-ionic heterocycles and features a beneficial common 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, 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, via 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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Extra info for Advances in Heterocyclic Chemistry, Vol. 19
Znd. (Milan) 54, 1105 (1972) [CA 78,97561e (1973)l; (c) A. Holm, N. Harrit, K. Bechgaard, 0. Buchardt, and S. E. Harnung, J. Chem. ,Chern. , 1125 (1972). ‘I6 38 W. D. OLLIS AND C. A. RAMSDEN [Sec. G The meso-ionic 1,3,2-oxathiazol-5-ones (169) show an interesting range of reactions with nucleophiles including ammonia, primary amines, and aqueous alkali. They also react with 1,3-dipolarophile~,~~~ including dimethyl acetylenedicarboxylate and methyl propiolate, yielding isothiazoles (17 1) and carbon dioxide.
They are prepared from N-acyl-N-(alkyl or ary1)-hydrazines (147, X = 0) or their hydrochlorides and carbonyl ~ h l o r i d e . ~ ~The - ~ Oisosyd~ n 9sM. Ohta and M. Sugiyama, Bull. Chem. Jap. 36, 1437 (1963). (a) H. Kato, T. 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.
Sub~equently~~ this mesoionic intermediate was trapped using 1,3-dipolarophiles. 2-Benzoyl-1,2dihydroisoquinaldonitrile (8 1) and tetrafluoroboric acid gave the Reissert salt (82), which with dimethyl acetylenedicarboxylate gave the product 83, R1 = R2 = CO,Me, and with ethyl phenyl propiolate yielded the primary adduct (84) and a secondary product (83, R1= C0,Et; R2 = Ph). 54Similarly, this nitrile (86, R1= R2 = Ph; R3 = H) and acetyl or benzoyl perchlorate give the 1,3-oxazolium perchlorates (85, R1= R2 = Ph; R3 = H; R4= MeCO or Ph .