Advances in Heterocyclic Chemistry, Vol. 18 by A.R. Katritzky, A.J. Boulton (Eds.)

By A.R. Katritzky, A.J. Boulton (Eds.)

(from preface)The current quantity features a wide variety of heterocyclic chemistry. Syntheses of heterocycles from thioureas are reviewed via T. S. Griffin, T. S. Woods, and I). L. Klayman, whereas eight. W. Schneller describes the chemistry of benzothiins and their derivatives (thiochromans. thiochromones, and thio-chromanones). advancements in chrom-3-ene chemistry are reviewed by way of L. Merlini. F. D. Popp contributes a bankruptcy at the isatins. A dialogue of theoretical elements of the tautomerism of pyrimidines, through J. S. Kwiatkowski and B. Pullman, follows up a corresponding past contribution (Vol. thirteen) on tautomeric purines. within the ultimate bankruptcy P. and D. Cagniant describe the ordinary prevalence ami synthesis of the bcnzofurans.

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B. To~ric~hin, 1. S. , and E. A. Org. Khzna. 8 , 1791 (1971). 40‘1 A. H. Tomchin, Y. A . Kharit, and A. K. Kutscnko, K h m . Farm. Zh. 7, 10 (1973). 402 36 [Sec. C FRANK D. 407 The cyclization of certain 2-substituted isatin derivatives were studied so as to compare them with the above cyclizations. 408 In contrast t o (126) X = S (127) X = 0 (130) 405 (128) X = S (129) X = 0 (131) I. S. , A. B. Tomchin, and E. N. Zhultova, Zh. Obshch. Khim. 39, 2339 (1969). H. King and J . Wright, J . Chenz. , 2314 (1948).

257 258 24 [Sec. A FRANK D. POPP i s a t i n - 3 - 0 x i m e , ~i s~a~t i, n~ -~3~- h y d r a ~ o n e3-phenyliminoo~indoles,~~~ ,~~~ 3-ben~ylideneindol-2(3H)-ones,~~~ l-(chl~roacetyl)isatin,~~~ and a variety of isatin derivatives 261 has been studied. A polarographic study of the alkaline hydrolysis of an isatin anil has been carried An analytical procedure for organotin hydrides has been based on the reduction of isatin t o o x i n d ~ l e . ~ ~ ~ VII. Reactions with Ketone Reagents A. 2755-Bromoisatin-3-oxime 0 1 (72) (73) has been prepared by reaction of 5-bromooxindole with sodium nitrite in acetic acid276and further examples of this reaction are included in Section II,C.

Heterocycl. Chem. 8, 313 (1971). 4Q7 H. E. Baunigarten and P. L. Creger, J . Amer. Chem. SOC. 82,4634 (1960). 498 J. Bergman, Acta Chem. Scand. 25, 1277 (1971). 499 M. C. Bettembourg and S. David, Bull. SOC. Chim. , 772 (1962). 5 0 0 B. Mills and K. Schofield,J . Chem. , 558 (1961). 601 S. Sarel and J. T. Klug, Isr. J . Chem. 2 , 143 (1964). 494 Sec. A] 47 THE CHEMISTRY O F ISATIN N-methylisatin 5 0 2 , 6 0 3 has been reported to give the N-substituted 2 3 diphenylindoxyl ( 179) and 3,3-diphenyloxindole (180) rather than epoxides as claimed1 earlier.

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