By A. R., & A. J. Boulton (Eds), Katritzky
(from preface)The 10th quantity of this serial ebook contains six chapters, 4 of which take care of the final chemistry of a particular workforce 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 considering 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 overseas taste of the ebook is preserved: our individuals come from six international locations in 3 continents.We thank the authors and publishers for his or her cooperation which has allowed creation of this quantity in below three hundred and sixty five days.
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Additional info for Advances in Heterocyclic Chemistry, Vol. 10
Khimiya, Moscow, 1965. 106 [Sec. VI. ] 23 BENZOFUROXANS of its derivatives,110-112leading to nitroamines, naphthofurazans, or 1,2-naphthoquinone dioxime derivatives, depending upon the conditions. Curious products isolated by Bailey and Evans from the reaction of benzotrisfuroxan with triphenyl phosphine have been examined by X-ray crystallography by Cameron and Prout. OPPh:, N--d (44) =PPha NO2 N II PPh3 (46) (45) D. MISCSLLANEOUSREACTIONS A variety of enamines1l6and enolate anionsll’ have been found to react with benzofuroxan, giving quinoxaline di-N-oxides in moderate yields [Eq.
VII. ] A. J. BOULTON AND P. B. GHOSH For rearrangements involving the heterocyclic ring, see Sections 11; 111,C; and VIII. VII. Reactions of the Homocyclic Ring A. ELECTROPHILIC ATTACK Nitration proceeds readily in benzofuroxan, giving first the 4-nitro, then the 4,6-dinitro compound. 5-Nitrobenzofuroxan, according to Drost,'18 is nitrated further in the adjacent 6-position. Bailey and Casez2reported that the major product is the 4,6-dinitro compound, but they did succeed in isolating a small amount of the 5,6-dinitro derivative from the reaction.
Mizianty, J . Org. Chem. 2 9 , 2 0 3 0 (1964). 22 T. E. Young and M. F. Mizianty, J . Med. Chem. 9, 635 (1966). Oddo, Gazz. Chim. Ital. 44, 482 (1914);Chem. Abstr. 8 , 3019 (1914). 18 46 R. A. HEACOCK AND s. KA~~PAREK [Sec. 111. 11 and Reich obtained a Grignard reagent from 5-bromo-1,3-dimethylindole which appeared to behave normally on oxidation or carbonat i ~ n . ~ ~ 111. Reactions of the Indole Magnesium Halides A. GENERAL COMMENTS I n some instances the reactions of the indole Grignard reagents resemble those of simple aryl or alkyl magnesium halides, but in many cases they appear to react anomalously.