Advances in Heterocyclic Chemistry, Vol. 10 by A. R., & A. J. Boulton (Eds), Katritzky

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

(from preface)The 10th quantity of this serial booklet contains six chapters, 4 of which care for the overall chemistry of a particular crew of heterocyclic compounds: pyridopyrimidines (W. J. Irwin and D. G. Wibberley), benzofuroxans (A. J. Boulton and P. B. Ghosh), isoindolee (J. D. White and M. E. Mann), and pyrylium salts (A. T. Balaban, W. Schroth, and G. Fischer). the remainder chapters are all in favour of indole Grignard reagents (R. A. Heacock and S. Kasparek) and with cyclic hydroxamic acids (J. B. Bapat, D, St. C. Black, and R. C. Brown).The foreign style of the ebook is preserved: our members come from six international locations in 3 continents.We thank the authors and publishers for his or her cooperation which has allowed construction of this quantity in below 12 months.

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5, 2638 (1911). 3 B. Oddo, Gazz. Chim. Ital. 39, 649 (1909); Chem. Abstr. 5, 686 (1911). 43 44 R. A. HEACOCK AND s. KASPAREK [Sec. 1 The indole Grignard reagents have been widely employed as intermediates in synthetic work, mainly for the introduction of substituents into the 1- or 3-positions of the indole ring system. ’ I n 1954, two summaries of the chemistry of the indole Grignard reagents were published (Sumpter and Millera and Kharasch and Reinmuthg). I n view of the importance of these compounds in indole chemistry and since there is no adequate modern survey of this field, an attempt has been made to review comprehensively the chemistry of the indole Grignard reagents.

Sao Paulo) 4, 183 (1937); Chem. Abstr. 32, 549 (1938). 6 Q . Mingoia, Boll. Chim. Farm. 77, 337 (1938);Chem. Abstr. 32, 7035 (1938). 7 S. T. Yoffe and A. N. Nesmeyanov, “Handbook of Magnesium Organic Compounds,” Vols. I, 11, & 111. Pergamon, Oxford, 1956. 4B. 8 W. C. Sumpter and F. M. Miller, “Heterocyclic Compounds with Indole and Carbazole Systems,” p. 50. Wiley (Interscience),New York, 1954. M. S. Kharasch and 0. ” Prentice-Hall, Englewood Cliffs, New Jersey, 1954. [Sec. 1 THE INDOLE GRIGNARD REAGENTS 45 halide, usually ethyl(or methy1)magnesium iodide(or bromide) in ether.

51, 17878 (1957). 36 M. Nakazaki, Bull. Chem. Soc. Japan, 32, 838 (1959); Chem. Abstr. 54, 13096 34 35M. Nakazaki, (1960). 50 R. A,. HEACOCK AND s. KA~PAREK [Sec. 111. , eserine (22)]molecule, which involve indole Grignard reagents as intermediates, have been described. Hoshino and his co-workers reported that treatment of the Grignard reagent obtained from tryptamine (23),by the action of a suitable alkyl magnesium halide, with methyl iodide in benzene did not give the expected indolenine derivative 24; instead dinordeoxyeseroline (25)was ~ b t a i n e d .

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