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

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

ISBN-10: 0120206099

ISBN-13: 9780120206094

(from preface)The 9th quantity of Advances in Heterocyclic Chemistry comprises 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 kind of brief synopses.Thanks are as a result Editorial Board, the writer, and the authors for his or her cooperation.

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(from preface)The 9th quantity of Advances in Heterocyclic Chemistry comprises 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.

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MONOAZAINDOLES: THE PYRROLOPYRIDINES 45 This sequence is useful for preparing compounds inaccessible by other routes. It does, however, require reduction of the parent azaindole, obtained by one of the previously described methods. Also, it has been tried only on the 7 isomer, and it was reported that 5-azaindole is more resistant to reduction. l8 The most significant contributions to this approach have been made by Russian workers. Yakhontov and R u b t ~ o vin , ~1960, ~ reported a new type of ring closure by heating 2,6-dichloro-3-(%chloroethyl)-4picoline (49, Scheme 4) with secondary amines in chlorobenzene in sealed tubes to give 4-methyl-7-azaindolines (50).

W. Holt, J . Chem. ,1313 (1953). 4 1 S. Okuda and M. M. Robison, J . A m . Chem. 81, 740 (1959). 42 F. G. Mann, A. F. Prior, and T. J. Willcox, J . Chem. , 3830 (1959). 43 T. R . Govindachari, S. Rajappa, and V. Sudarsanam, Tetrahedron 16, 1 39 (1961). R. A. Abramovitch and K. A. H. A d a m , Can. J . Chem. 40, 864 (1962). 45 A. H. Kelly, D. H. McLeod, and J. Parrick, Can. J . Chem. 43, 296 (1965). 46 A. H. Kelly and J. Parrick, Can. J . Chem. 44, 2455 (1966). 47 L. N. Yakhontov, E. V. Pronina, and M.

Nat. [6] 5 , 303 (1927);Chem. Abstr. 21, 1814 (1927). p. 171-172') was prepared, but was recovered unchanged after heating with polyphosphorio acid at 200'. 57 C. Rath, Ann. Chem. 486, 95 (1931). 55 SEC. 111. ] MONOAZAINDOLES: THE 39 PYRROLOPYRIDINES (28) (27) hydrazones failed to react. The N-methyl- and N-phenyl-quinol-4-one hydrazones failed to cyclize under a variety of conditions, including polyphosphoric acid, zinc chloride, and boron trifluoride. 50,51 @yo / (30) (29) Isopropyl methyl ketone 2-pyridylhydrazone and 3-pyridylhydrazone on heating with zinc chloride gave 2,3,3-trimethyl-7-azaindolenine (31)50and 2,3,3-trimethyl-4-azaindolenine (32)51in 29 and 23 %yields, respectively.

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


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