By Gribble Gordon W. and Joule John A. (Eds.)
This can be the 16th annual quantity of growth in Heterocyclic Chemistry, and covers the literature released in the course of 2003 on many of the very important heterocyclic ring systems.This quantity opens with really expert experiences. the 1st covers 'Lamellarins: Isolation, job and synthesis' an important staff of biologically energetic marine alkaloids and the second one discusses 'Radical Additions to Pyridines, Quinolines and Isoquinolines'. the remainder chapters research the hot literature at the universal heterocycles so as of accelerating ring measurement and the heteroatoms current.
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Additional info for A critical review of the 2003 literature preceded by two chapters on current heterocyclic topics
Nagata, T. Furuta, T. Yokokura, T. Miyasaka, Chem. Pharm. Bull. 1991, 39, 3183. A. S. Sherburn, Tetrahedron 1991, 47, 4077. B. K. Pennell, F. Ujjainwalla, J. Chem. , Chem. Commun. 1992, 1067. F. Minisci, F. Fontana, T. Caronna, L. Zhao, Tetrahedron Lett. 1992, 33, 3201. F. Minisci, F. Fontana, G. M. Yan, J. Org. Chem. 1993, 58, 4207. C. Harrowven, Tetrahedron Lett. 1993, 34, 5653. H. Togo, K. Hayashi, M. Yokoyama, Bull. Chem. Soc. Jpn. 1994, 67, 2522. 1986, 51,4411. C. Harrowven, R. Browne, Tetrahedron Lett.
Ipso-substitution has been shown to occur when 2,4-dicyanopyridine 74 and tetrabutyltin are irradiated at 254 nm, with butylated cyanopyridines 75 and 76 being formed in 42% and 34% yield respectively <92TL3201>. It has been suggested that the reaction proceeds by an electron transfer from tetrabutyltin to the photo-excited pyridine 77, as indicated in Scheme 26. CN ~ CN ~~,]N ~ 77 / 74 * CN CN Bu4Sn' MeCN hv'~ ~~'ININ~ + ~'~L ~ + 74, CN Bu CN 75,42% 76, 34% ~HCN ~HCN CN Bu4Sn'H+. u" + ~ C - Bu Bu3Sn+ H 78 FBu CN CN 79 20% CN 1 Bu H CNJ 80 Scheme 26 The scope of the reaction has yet to be established and may prove rather limited.
4 Radical Halogenation Radical chlorination of pyridine has been achieved in reasonable yield <96CHECII84>, with photolysis of a carbon tetrachloride solution of pyridine and chlorine facilitating efficient t~-chlorination <67JHC375>. Bromination has been effected in the vapour phase with BrC1 and gives mainly 2-bromopyridine. By contrast, when Br2 was used both 2- and 3-bromopyridine were given in roughly equal quantity <67JHC377>. 5 Radical Silylation Applications of the reaction in medicinal chemistry have begun to surface, in particular for the preparation of camptothecin derivatives.