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 includes six chapters, 4 of which take care of the final chemistry of a selected staff 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 focused on 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 e-book 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 construction of this quantity in under 365 days.

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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 . 41, recently shown that the Grignard reagent derived from 2-methyltryptophol undergoes an analogous reaction with methyl iodide; the I H (32) R = H (35) R = CH3 (33) R (34) R = = H CH3 37 T.

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.

516, 7 6 (1935). 40 T. Hoshino and T. Kobayashi, Ann. Chem. 520, 11 (1935). 4 1 T. Hoshino, Proc. Imp. Acad. (Tokyo) 10, 159 (1934) ; Chem. Abstr. 28, 5439 38 (1934). 42 T. Hoshino and K. Shimodaira, Ann. Chem. 520, 19 (1935). [SeC. 111. 43 2. Alkenyl Halides It is only in relatively recent years that the interaction of indole Grignard reagents with unsaturated aliphatic halogen compounds has (36) (38) (39) (40) (41) (43) (44) (45) (46) (47) (48) R = R’ = H ; R” = CHzCH=CHz R = CHzCH=CHz; R’ = H ; R” = CH3 R = H ; R’ = CHzCH=CHz; R” = CHs R = CHzCHzCH3; R’ = H ; R” = CH3 R = H; R’ = CHzCHzCH3; R” = CH3 R = H ; R’ = CH3; R“ = CHzCHzCH3 R = H ; R’ = CHs; R” = CH&H=CHz, R = CHzCHzCHzCHs; R’ = H ; R” = CH3 R = H ; R’ = CHzCHzCHzCH3; R” = CH3 R = CHzCH&H(CHs)z;R’ = H ; R” = CH3 R = H ; R’ = CH&HzCH(CH3)2; R“ = CH3 MiH=CHz ‘ d (37) R = H (42) R = C H 3 been studied.

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