Get Advances in Heterocyclic Chemistry, Vol. 9 PDF

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

ISBN-10: 0120206099

ISBN-13: 9780120206094

(from preface)The 9th quantity of Advances in Heterocyclic Chemistry contains surveys of the chemistry of the subsequent teams of heterocyclic compounds: 1,2,5-thiadiazoles (L. M. Weinstock and P. I. Pollack); 1,3,4-thiadiazoles (J. Sandstrom); pyridazines (M. Tisler and B. Stanovnik); Reissert compounds (F. D. Popp); phenothiazines (C. Bodea and that i. Silberg); and pyrrolopyridines (R. E. Willette).Suggestions are welcomed for contributions to destiny volumes; they need to be within the type of brief synopses.Thanks are as a result of the Editorial Board, the writer, and the authors for his or her cooperation.

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111. 1 13 REISSERT COMPOUNDS 0 qN 0 m - o - ( ! - C6H5 c6H5 H-C-0-C- I1 C6H5 I CBH5 (30) (29) benzene34 or sodium hydride in dimethylformamide a t room temperaturez7)gave 30. 33 A similar mechanism can be used for the formation of 30. It is of interest to note that in this case reaction of the anion (19) of the quinoline Reissert compound takes place in the 2-position. A wide 30,33-39 ranging from f ~ r m a l d e h y d eto ~~ variety of aldehydes', d i a l d e h y d e ~37~ have ~ , been used. 33 The condensation of the anion of 26 with the appropriate aldehyde has played a n important part in the convenient synthesis of a number of alkaloids and alkaloid-related materials such as calycotomine (33),38papaverinol (34),sarmepavine (24),2gand 0-methyldauricine "9 H.

Chem. , 603 (1945). 22 M. M. Robison and B. L. Robison, J. Am. Chem. SOC. 77,457 (1955). 23 A. Albert and R. E. Willette, J. Chem. , 4063 (1964). 24 R. E. Willette, unpublished results (1966). 13 G. 14 SEC. 111. ] MONOAZAINDOLES : THE PYRROLOPYRIDINES 31 ethoxide a t 290" for 10 minutes to give 2-methyl-6-azaindole (6, R =Me) in 23 yoyield. Similarly, Clemo and Swanz1 synthesized 7-azaindole (2) and its 2-methyl and 2-ethyl derivatives in low yields (3, 17, and l a % , respectively). They failed to improve the yield by use of potassium g"" NaOEtt N\ NHCOR 290' >T'--J, R N\ H "aM" -NQ)-lNHCOR (9) H R (10) ethoxide, which Tysonz6 reported to give a higher yield of indole.

R. K. Murty, J . Org. Chem. 26, 122 (1961). 111. l5*16a Initially, consistent yields (50-63 yo)of 7-azaindole were obtained on a 3-mole scale by employing several modifications including the use of mineral oil as a diluent. These workers established the mechanism of the cyclization (Scheme 1) when sodium anilide is used as the base. A yield of 52 % was obtained when the formimidate (16) was heated a t 200" with sodium N-methylanilide, forming amidine 14 R = Me and preventing tautomerization PhNH NHCHO m N=CH-NPh (15) SCHEME 1 to amidine 13 and formation of ion 15.

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Advances in Heterocyclic Chemistry, Vol. 9 by A.R. Katritzky, A.J. Boulton (Eds.)

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