Download Advances in Heterocyclic Chemistry, Vol. 26 by A.R. Katritzky, A.J. Boulton (Eds.) PDF

By A.R. Katritzky, A.J. Boulton (Eds.)

(from preface)Volume 26 comprises 3 chapters. C.A.Ramsden reports heterocy-clic betaines derived from 6-membered heteroaromatic earrings. those compounds were intensively studied over the last 10 years and feature no longer formerly been comprehensively reviewed. O. Meth-Cohn and B. Tarnowski summarize the chemistry of the thiocoumarins, a a bit overlooked crew of heterocycles. ultimately, W. Friedrichsen has reviewed the chemistry of the benzo[r]furans which, not like the aza and thia analogs, haven't formerly been thought of during this sequence. right here back we've a bunch of compounds the chemistry of which has complicated significantly during the last decade.

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W. Dilthey and H. Dierichs, J . Prakr. Chem. 144, I (1936).

The benzotriazinium iodides (271) so formed are readily deprotonated by base giving the betaines (269; R' = alkyl, R2= aryl). In the presence of sodium ethoxide, alkylation of benzotriazines 270 occurs at positions 2 and 3. The bright red betaines 269 form salts with dilute hydrochloric acid and are dealkylated by hot ethanolic potassium hydroxide. The mesomeric betaine structure (269)is fully supported by spectroscopic properties. 96-198 15. 1,2,3-Benzotriazinium-4-thiolates (272) Betaines 272 have been made by (i) treatment of 1,2,3-benzotriaziniurn4-olate (261) (Section III,B, 13) with phosphorus pentasulfide and (ii) glycosidation of the sodium salt of 4-mercapto-l,2,3-benzotriazine(273; R = H) using 2,3,4,5-tetra-O-acetyl-c~-~-glucopyranosyl bromide.

Ptrkin I , 2338 (1976). 62 J . Banerji, N. Dennis, A. R. Katritzky. R. L. Harlow. and S . H. Simonsen. J . Cbem. Res. 38 (1977); J. Cbrni. R P . 517 (1977). 6 3 T. Lierum and K. Undheim. Actu Cbetn. S c u d . , Ser. -0. Ranger, G . A. Ulsaker, and K. ,70. 64 A. Mori, S. Ohta, and H. Takeshita. Heterocycles 2,243 (1974); H. Takeshita, A. Mori, and S. Ohta, Bull. Cbem. Soc. Jpn. 47, 2437 (1974). 6 5 A. R. Katritzky and Y . Takeuchi, J . A m . Chem. Soc. 4134 (1970). 66 A. R. Katritzky and Y. Takeuchi, J.

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