By A.R. Katritzky, A.J. Boulton
(from preface)This quantity comprises articles which raise so far older stories within the sequence. development within the chemistry of the 1,3-oxazines because they have been lined through Eckstein and Urbariski in quantity 2 (1963) is defined by way of an identical authors. Acheson and Elmore evaluate reactions of acetylenecarboxylic esters with nitrogen heterocycles, which were the topic of a lot focused learn within the years on the grounds that Acheson's article in quantity 1. The overview on indolizines (Swinbourne, Hunt, and Klinkert) additionally concentrates at the advances of the final 15 years and up-dates studies released in other places. Anastassiou and Kasmai supply a severe 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
French Patent 1,585,475 [CA 74,42365 (1971)l.
Chem. Soc. 94,1354 (1972). me S. M. Kupchan, Y. Komoda, G. J. Thomas, and H. P. J. Hintz, 1. Chem. , Chem. , 1065 (1972). A. I. Meyers, C. C. Shaw, D. Home, L. M. Trefonas, and R. J. , 1745 (1975). 275 Sec. 21 51 1,3-OXAZINE DERIVATIVES and Calubrinol acetate, isolated by Wani et ~ 1 . from ~ ' ~ Calubrina texennsis. Maytenus macrolides are represented by formula 122; R is Me, Et, and i-Pr in Maytansine, Maytanprine, and Maytanbutine, respectively. Calubrinol differs from Maytansine only by the presence of an additional hydroxy group and this is acetylated in Calubrinol acetate.
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.
Advances in Heterocyclic Chemistry, Vol. 23 by A.R. Katritzky, A.J. Boulton