Advances in Heterocyclic Chemistry, Vol. 23 by A.R. Katritzky, A.J. Boulton

By A.R. Katritzky, A.J. Boulton

(from preface)This quantity includes articles which increase to this point older experiences within the sequence. growth within the chemistry of the 1,3-oxazines when you consider that they have been coated by way of Eckstein and Urbariski in quantity 2 (1963) is defined by means of a similar authors. Acheson and Elmore evaluation reactions of acetylenecarboxylic esters with nitrogen heterocycles, which were the topic of a lot focused learn within the years considering 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 experiences released somewhere else. Anastassiou and Kasmai supply 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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French Patent 1,585,475 [CA 74, 42365 (1971)]. C. Giordano, G. Ribaldone, and G. Borsotti, Synrhesis, 92 (1971). B. A. Arbuzov, N. N. Zobova, F. B. Balabanova, and M. F. Tarasova, IN. Akad. Nauk SSSR, Ser. , 2324 (1972). lac Sec. RIVA"IVES 21 N-Hydroxymethyl amides are potential a c y l i m i n e ~ ' ~and ~ - ~react ~~ in a strongly acid medium (usually acetic and sulfuric acids) at ca. lS7-168 Another general method, mentioned in our earlier review,' of formation of 5,6-dihydro-4H-l,3-oxazinesis the reaction of 3-azidopropanol and aromatic aldehydes.

The method involves Diels-Alder-type addition of N-acylimines with oiefins. N-Acylimines are rather unstable but they possess electrophilic character and react with nucleophilic dienophiles, such as e n a m i r ~ e s , ~ yielding ~ ' - ~ ~ ~43 [Eq. (31)]. ~ ~ ~ ~ ~ ~ ~ H. Witte and W. Seeliger, Angew. Chem. 84, 343 (1972). H. J. Kiefer, Ger. Offen. 2,049,160 [CA 77, 19655 (1972)l. l'' R. R. Schmidt and E. Schlipf. Chem. Ber. 103, 3783 (1970). N. P. Gambaryan and Yu. V. Zeifman, Izv. Akad. Nauk.

A. 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.

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