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 final chemistry of a particular team 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 rest chapters are desirous 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 taste of the ebook is preserved: our participants come from six nations 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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Extra resources for Advances in Heterocyclic Chemistry, Vol. 10
2) tionlooshowed that the spectral changes occurring on acidification of the latter compound are not reversible, suggesting that decomposition had taken place. Quaternization is difficult; benzofuroxan is unaffected by triethyloxonium fluoroborate. 101,lola B. ' O 2 4-Nitro- and 4,6-dinitrobenzofuroxan are unaffected by this reagent, whereas the 5-chloro and 5-methoxy compounds are destroyed. lo2 Milder reagents (performic, peracetic acids) do not oxidize benzofuroxans. 22 C. REDUCTION The reduction of benzofuroxans can lead to a variety of products, depending upon the conditions.
H. 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.
L. Julian and J. Pikl, Proc. Indiana Acad. Sci. 45, 145 (1935); Chem. Abstr. 31, 1026 (1937). 27 A. H. Jackson and P. Smith, Tetrahedron, 24,2227 (1968). 25 48 R. A. HEACOCK AND s. KA~PAREK [Sec. 111. , 170"-172",32 152",33and 214"30,33)for 3,3-dimethylindolenine (12) have been reported. Hoshino reported that the melting point of the compound described as 3,3-dimethylindolenine (12) was initially 185"-186", but this changed t o 160"-210" on recrystallization; the change in melting point was accompanied by an apparent increase in molecular weight by a factor of three.