By A.R. Katritzky, A.J. Boulton
(from preface)This quantity includes articles which raise up to now older studies within the sequence. development within the chemistry of the 1,3-oxazines considering the fact that they have been lined by means of Eckstein and Urbariski in quantity 2 (1963) is defined by means of an analogous authors. Acheson and Elmore assessment reactions of acetylenecarboxylic esters with nitrogen heterocycles, which were the topic of a lot targeted examine within the years on account that Acheson's article in quantity 1. The assessment on indolizines (Swinbourne, Hunt, and Klinkert) additionally concentrates at the advances of the final 15 years and up-dates stories released somewhere else. Anastassiou and Kasmai offer a serious account of the ''тг-excessive heteroannulenes,'' and Fletcher and Siegrist deal authoritatively with the olefin-forming condensations of anils with methyl teams, the ''Anil Synthesis.''
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Extra resources for Advances in Heterocyclic Chemistry, Vol. 23
Adickes, I. R. Politzer, G. R. Malone, A. C. Kovelesky. R. L. Nolen, and R. C. Portnoy, J. Org. Chem. 38 36 (1972). Sec. 11 1,3-OXAZINE DERIVATIVES 35 1. Synthesis of Aldehydes The ring opening of tetrahydro-I ,3-oxazines to aldehydes has recently found wide application through the work of M e y e r ~ . ~ tetrahydro-1 ,3-oxazinesY prepared from the readily available 5,6dihydro-4H-lY3-oxazines, possess strong nucleophilic properties and can react with alkyl halides and carbonyl compounds. 3-22,223 by alkyl halides to 75, and the product can be reduced with aqueous sodium borohydride (or borodeuteride) at pH 7 in tetrahydrofuranethanol-water at - 35" to - 45°C to tetrahydro-I ,3-oxazines (76) in quantitative yield.
F. Eiden and B. S . Nagar, Naturwissenschaften 50, 403 (1963). E. Steglich, Angew. Chem. 86, 414 (1974). Steglich, E. Buschmann, and 0. Hollitzer, Angew. Chem. 86, 594 (1974). N. D. Bondarchuk, V. V. Mamot, L. A. Lazuhina, G. V. Petetskaya, and V. P. Kukhar, Zh. Org. , 10,735 (1974). H. B. Kagan and Y-H. Bull. Soc. Chim. , 1819 (1966). G . Meier, Angew. , Znt. Ed. Engl. 13, 425 (1974). A. Krantz and B. Hoppe, J . Am. Chem. 97, 6590 (1975). T. Sasaki, K. Kanematsu, and A. Kakehi, J. Org. Chem. 36, 2451 (1971).
A. I. Meyen, A. Nabeya, H. W. Adickes, I. R. Politzer, G. R. Malone, A. C. Kovelesky. R. L. Nolen, and R. C. Portnoy, J. Org. Chem. 38 36 (1972). Sec. 11 1,3-OXAZINE DERIVATIVES 35 1. Synthesis of Aldehydes The ring opening of tetrahydro-I ,3-oxazines to aldehydes has recently found wide application through the work of M e y e r ~ . ~ tetrahydro-1 ,3-oxazinesY prepared from the readily available 5,6dihydro-4H-lY3-oxazines, possess strong nucleophilic properties and can react with alkyl halides and carbonyl compounds.