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 ebook contains six chapters, 4 of which take care of the overall chemistry of a selected 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 enthusiastic about 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 nations in 3 continents.We thank the authors and publishers for his or her cooperation which has allowed creation of this quantity in under twelve months.

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Nakazaki and S. hoe, Nippon Kagaku Zmshi 76, 1159 (1955); Chem. Abstr. 51, 17877 (1957). 46 N. Lerner, Dia8ertation Abstr. 24, 4982 (1964). 52 R. A. HEACOCK AND s. KAQPAREK [Sec. 111. 36 3-Allyl-3-methylindolenine (37) was also synthesized by the action of methyl iodide on 3-allylindolc magnesium iodide; however, the yield of 37 was not as good as that obtained in the procedure starting from 3 - m e t h ~ l i n d o l e . ~ ~ 2-Methyl-3-n-propylindole (43) was obtained by hydrogenation of the intermediate 2-methyl-3-allylindole (44), obtained by the allylation of 2-methylindole magnesium iodide.

Other electrophilic substitutions proceed with difficulty, or not at all. Nitrosation and diazo coupling require the presence of the strongly activating dimethylamino group (see Section VIII). Bromine adds, in the presence of sunlight, to give tetrabromotetrahydrobenzofuroxan (48) ; the initial attack is probably free-radical in nature. ^? 126a B . NUCLEOPIIILIC ATTACK Aniline and benzofuroxan react at high temperatures ( 150°-1600) to give 2,5-dianilinobenzoquinonedianil(49). ~~ 0- (49) Several examples of nucleophilic displacement of nitro-activated leaving groups have been recorded.

Boyer and S. E . Ellzey, J . Org. Chem. 24, 2038 (1959). 103 J. H. Boyer and S. E. Ellzey, J . Org. Chem. 26, 4684 (1961). 104 D. Dal Monte Casoni and E. Sandri, Ann. Chim. (Rome) 53, 1697 (1963). A. J. B. GHOSH 22 [Sec. VI. 86Naphtho[ 1,2-c]furoxan is reported to give the corresponding furazan with hydrazine. l8,lo’ The action of copper and hydrochloric acid produces o-nitroanilines in quantitative yield12* 39; with 5-methylbenzofuroxan both aminonitrotoluenes were obtained [Eq. (4)]. 12 389 I 0- (39%) (61%) Some internal oxidation-reduction reactions have been reported with the bisulfite adducts of naphtho[ 1 , 2 - c ] f u r o ~ a n and ~ ~ ~some -~~~ 106 J.

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