By Alan R. Katritzky
Meant for natural chemists, this quantity follows the layout of earlier volumes and gives up to date details on chosen components of heterocyclic chemistry.
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Additional resources for Advances in Heterocyclic Chemistry, Vol. 39
Lithium aluminum hydride in pyridine, lithium borohydride in THF, and sodium borohydride in ethanol all reduced 290 to ethyl 4-substituted-2-methylthio- I ,6-dihydropyrimidines (291). I5lThe intermediacy of the hexahydro derivative 293 was proved by its isolation from the reaction mixture and subsequent conversion to 294 with additional borohydride. l-Phenyl-4,4,6-trimethyldihydropyrimidine (292) may ring open via N-1 -C-2 or C-2-N-3 cleavage. In fact, only the former is observed, presumably a result of the increased stability of the N- I -phenyl anion.
IM Io5 Io6 'ol Io8 Io9 'lo J. A. Marshall and W. S. Johnson, J. Org. Chem. 28,421 (1963). R. F. Borch, M. D. Bernstein, and H. D. Durst, J. Am. Chem. Soc. 93,2897 (1971). G. W. Gribble, P. D. Lord, J. Skotnicki, S. E. Dietz, J. T. Eaton, and J. L. Johnson, J. Am. Chem. Soc. 96,78 12 (1974). G. W. Gribble and S. W. Wright, Heterocycles 19,229 (1982). G. W. Gribble and J. H. Hoffman, Synthesis, 859 (1977). J. G. Berger, F. Davidson, and G. E. Langford, J. Med. Chem. 20,600 ( 1 977). N. Umino, T. Iwakuma, and N.
In some cases, products 286/287 or 288 could be obtained exclusively by judicious choice of reaction conditions. Earlier reports by other workerPJ4*prompted these authors to attempt reductions of 285 with NBH in acetic acid. l~~ thione derivatives 288 ( X = S) did not react under these conditionsand were RZ R2 RZ I R’ (285) (2%) (287) P. Aeberli and W. J. Houlihan, J. Org. Chem. 34,2720 (1969). M. Tisler and B. Stanovnik, Adv. Heterocycl. Chem. 24,42 I ( 1979). 14’ C. Kashima, A. Katoh, Y. Yokota, and Y.
Advances in Heterocyclic Chemistry, Vol. 39 by Alan R. Katritzky