By A.R. Katritzky, A.J. Boulton (Eds.)
(from preface)Volume 26 includes 3 chapters. C.A.Ramsden studies heterocy-clic betaines derived from 6-membered heteroaromatic earrings. those compounds were intensively studied during the last 10 years and feature now not formerly been comprehensively reviewed. O. Meth-Cohn and B. Tarnowski summarize the chemistry of the thiocoumarins, a a little bit missed staff of heterocycles. eventually, W. Friedrichsen has reviewed the chemistry of the benzo[r]furans which, in contrast to the aza and thia analogs, haven't formerly been thought of during this sequence. the following back now we have a bunch of compounds the chemistry of which has complicated significantly during the last decade.
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(from preface)Volume 26 comprises 3 chapters. C. A. Ramsden reports heterocy-clic betaines derived from 6-membered heteroaromatic jewelry. those compounds were intensively studied during the last 10 years and feature now not formerly been comprehensively reviewed. O. Meth-Cohn and B. Tarnowski summarize the chemistry of the thiocoumarins, a a bit ignored crew of heterocycles.
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Additional resources for Advances in Heterocyclic Chemistry, Vol. 26
Nilsen and K . Undheim, Acfa Chern. , Ser. B 30,619 (1976). D. L. Garling and N. H. Crornwell. J . Org. Chem. 38, 654 (1973). K. Undheirn and P. E. Hansen, Chein. Scr. 3, 113 (1973). P. E. Hansen and K . Undheim, J. C . , Perkin I , 305 (1975). Sec. IILB] 31 HETEROCYCLIC BETAINES 0 1 0 SCHEME7. Reagents: i, ion-exchange resin; ii, Et,N; iii, hv; iv, AT; v, RiRZC=CH2; vi, R ' C z C R ' ; vii, EtO,CN=NCO,Et; viii, Mel: ix, Ag,O or NaHCO,. Acetylenes and diethyl azodicarboxylate give similar adducts (173 and 174)(Scheme 7).
Sackman, E. Shefter. and E. Vega, J . C. , Chem. , 680 (1972). K. Schofield and J. C. E. Simpson, J . Chem. , 512 (1945). D. E. Ames and H. Z. Kucharska, J . Chem. , 4924 (1963). D. E. Ames and H. Z. Kucharska, J . Chem. , 283 (1964). 1 5 6 D. E. Ames, J . Chem. , 1763 (1964). IS’ D. E. Ames, R. F. Chapman, and H. Z. Kucharska, J . Chem. , 5659 (1964). ”* D. E. Ames, R. F. Chapman, H. Z. Kucharska, and D. Waite, J . Chem. , 5391 (1965). 59 D. E. Ames and A. C. Lovesey, J . Chem. , 6036 (1965). D.
Ver. 18,43(1956). [CA 51. 5094(1957)]. 1 9 5 R. C. Kerber and P. J. Heffron, J . Org. Chem. 37, 1592 (1972). 17' I" Sec. B] 49 HETEROCYCLIC BETAINES 14. I ,2,3-Benzotriazinium-4-aminides (269) NR' NHAr NHAr Menschutkin alkylation of 4-arylamino- 1,2,3-benzotriazines (270) in ethanol occurs at the 2-position. 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.
Advances in Heterocyclic Chemistry, Vol. 26 by A.R. Katritzky, A.J. Boulton (Eds.)