By A.R. Katritzky, A.J. Boulton
(from preface)This quantity includes articles which raise thus far older reports within the sequence. growth within the chemistry of the 1,3-oxazines considering the fact that they have been coated through Eckstein and Urbariski in quantity 2 (1963) is defined via an analogous authors. Acheson and Elmore evaluation reactions of acetylenecarboxylic esters with nitrogen heterocycles, which were the topic of a lot focused study within the years due to the fact that Acheson's article in quantity 1. The evaluate on indolizines (Swinbourne, Hunt, and Klinkert) additionally concentrates at the advances of the final 15 years and up-dates experiences released in different places. Anastassiou and Kasmai offer 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 info for Advances in Heterocyclic Chemistry, Vol. 23
A new group of 1,3-oxazine derivatives is the azapyrylium salts with three double bonds, and they too will be described in a separate section of the present review. '@l H. L. Klopping and H. M. S. Patent 3,352,662 [CA 68, 114,610 (1968)l. J. D. Warren, J. H. MacMillan, and S. S. Washburnc, J. Org. Chem. 40,743 (1975). leP z. ECKSTEIN AND T. UREIA~~SKI 28 [Sec. l 1. Cyclizution Schmidt4 classified the synthetic routes to 1,3-oxazines with two double bonds as methods a, by and c of Fig. 3. Prior to Schmidt, only (4 (b) (4 FIG.
Arbuzov, N. N. Zobova, F. B. Balabanova, and A. V. Fuzhenkova, Dokl. Vses. Konf. Khim. Zh. Khim. 3 Zh 355 (1973)]. le7B. A. Arbuzov, N. N. Zobova, F. B. Balabanova, A. V. Fuzhenkova, and V. D. Pankratova, Izv. Akad. Nauk SSSR, Ser. , 1580 (1973). lea M. Lora-Tamayo, R. Madrofiero, G. G. Mufloz. Leipprand, Chem. Ber. 97, le4 lee 2234,2244 (1964). lee M. Lora-Tamayo, D. Gracian, and V. Gomez-Parra, Tetrahedron, Suppl. 8, Part I, 305 (1967). 30 2. ECKSTEIN AND T. URBAfiSKI [Sec. 201described an interesting cyclization that differs from methods a, b, and c.
Tomilov, Zh. Org. Khim. 10, 1164 (1974). m4 R. R. Schmidt and A. R. Hoffman, Chem. Ber. 107,78 (1974). le6 S. P. McManus and R. A. , 4549 (1973). lee S. P. McManus and D. , 4271 (1974). le7C. Monneret, P. Choay, and 0. Khuong-Huu, Tetrahedron 31, 575 (1975). z. ECKSTEIN AND 22 [Sec. 3 T. U R B A ~ ~ S K I 3. Reactions of bThione Derivatives Tetrahydro-I ,3-oxazine-2-thione reacts with rearrangement to yield 46 and a thiazinel" [Eq. (34)]. CIS + BT:,:;NH. sH + (34) c J N H ( C H n. 3 (46) Thione derivatives can be S-methylated.