By Gribble Gordon W. and Joule John A. (Eds.)
This is often the 16th annual quantity of growth in Heterocyclic Chemistry, and covers the literature released in the course of 2003 on lots of the very important heterocyclic ring systems.This quantity opens with really good reports. the 1st covers 'Lamellarins: Isolation, task and synthesis' an important workforce of biologically energetic marine alkaloids and the second one discusses 'Radical Additions to Pyridines, Quinolines and Isoquinolines'. the rest chapters study the new literature at the universal heterocycles so as of accelerating ring measurement and the heteroatoms current.
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Additional resources for A critical review of the 2003 literature preceded by two chapters on current heterocyclic topics
G. Banwell. L. Flvnn. E. Hamel. R. ~s. ('hem CornrnTm 1007 907 26 97T5951 97WO01336 98JOC7698 98JOC9139 98JOM165 98T5075 98WO50365 99AG(E)1435 99AJC755 99JA54 99JMC 1901 99JNP419 99T14515 99T6555 99TL4177 99TL9085 99WO67250 00JOC2479 00JOC3587 00MI1147 01MI1403 01S1164 01TL1205 02BMC3285 02JA11250 02JNP500 02MI163 02OL2633 02T6373 02TL9437 03CR7392 03OL2959 03PHC140 03TL1363 03TL4443 04AG(E)866 04BMC1697 04JOC0000 04QSAR61 04T0000 04T0000 04WO014917 P. Cironi, F. Albericio and M. Alvarez F. Ishibashi, Y.
Sutton The reaction was shown to be triggered by protonation of the ketone and reduction to 139. Cyclisation of the carbon centred radical to the pyridinium ring next produced radical cation 140. Addition of a second electron then gave enamine 141, which underwent reversible protonation to iminium salt 138. Further cathodic reduction completes the sequence (Scheme 38). Interestingly, such cyclisations appear to be reversible as the product mixtures attained better reflect a reaction under thermodynamic control than one under kinetic control <03EJO2919>.
In each of the aforementioned examples, overall yields were typically less than 30% based on the phenyl radical source and below 5% based on pyridine. Regioselectivity was also poor, though many early reports suggested otherwise. Reassessments of the isomer distribution using spectroscopic methods led Hey e t al. <55JCS3963, 60JCS3787> and Dannley and Gregg <54JA2997> to conclude that each method gave a similar product distribution with 2-, 3- and 4-phenylpyridine being formed in a ratio of ca.
A critical review of the 2003 literature preceded by two chapters on current heterocyclic topics by Gribble Gordon W. and Joule John A. (Eds.)