Download Advances in Heterocyclic Chemistry, Vol. 9 by A.R. Katritzky, A.J. Boulton (Eds.) 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 next 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 because of the Editorial Board, the writer, and the authors for his or her cooperation.

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Example text

Moller, Ann. Chem. 599, 233 (1956). 52 K. Moller and 0. Sus, Ann. Chem. 612, 153 (1958). 1 MONOAZAINDOLES : THE PYRROLOPYRIDINES 35 The reaction sequence involves refluxing the appropriate 4-hydroxynaphthyridine in concentrated nitric acid, followed by reduction of the nitro compound over Raney nickel at room temperature and HOzC H (24) H SCHEME 3 atmospheric pressure. The amine is diazotized with sodium nitrite in N-hydrochloric acid at O”, taking the reaction mixture rapidly to dryness at low temperature.

Elliott, Jr. B. McGriff, J . Org. Chem. 22, 514 (1957). R. F. Collins and T. Henshall, J . Am. Chem. 80, 159 (1958). V. ] REISSERT COMPOUNDS 19 The proton magnetic resonance spectrum of I-cyano-l,2-dihydroisoquinaldonitrile (8) has been reported40 and is consistent with the assigned structure. A report on the long-range proton coupling in Reissert compounds has appeared. 49a V. Related Compounds and Reactions In many cases compounds analogous to Reissert compounds have been reported. No attempt will be made to describe all such reactions in this review, but rather the coverage will be restricted to those in which some direct comparison t o 1 and 2 has been or can be made.

Am. Chem. SOC. 80, 1181 (1958). 111. 4. F. D. 29-30 This advantage was noted despite the need of additional synthetic steps to convert the carbinol ester to a methylene group. 37I n the quinoline series the product has been converted to a compound having curariform activity. 33It should be pointed out, however, that the expected tertiary alcohols are available by reaction of Grignard reagents with Reissert compounds as noted below. 4. l Thus 19, (R=C,H,) could give rise to 35 or 36 (R from RMgX).

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