By P. N. Preston
The Chemistry of Heterocyclic Compounds, in view that its inception, has been famous as a cornerstone of heterocyclic chemistry. each one quantity makes an attempt to debate all features – homes, synthesis, reactions, physiological and business value – of a selected ring process. to maintain the sequence updated, supplementary volumes masking the hot literature on each one person ring process were released. Many ring platforms (such as pyridines and oxazoles) are handled in unique books, every one which include separate volumes or components facing assorted person themes. With all authors are well-known specialists, the Chemistry of Heterocyclic Chemistry is taken into account world wide because the integral source for natural, bioorganic, and medicinal chemists.
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Additional resources for Benzimidazoles and Cogeneric Tricyclic Compounds, Part 2 (The Chemistry of Heterocyclic Compounds, Volume 40)
The acid-catalyzed cyclization of N-(2-benzamidophenyl)pyrrolidin-2-one is reporteds6 to afford 2,3-dihydro- 1H-pyrrolo[1,2-a]benzimidazole, albeit in unspecified yield. 74)]. 9). 74; R ' = H , R 2 = N 0 2 ) is consideredm to be initiated by Curtius rearrangement in a sulfonyl nitrene intermediate. 71; R' = H, R2 = C0,Et. R2 = Me) = R2 = H) = R2 = H) = R' = H) = R2 = H) = R2 = H)' R' = H, R2 = Cl) R' = H, R2 = Br) R' R' R' R' R' 8 8 z. - -e - 71 50 quant. p. ("C) b b b b d Benzene-n-hexane b - Cyclohexane Ether -b 52 53 54 54 51 58 58 58 58 58 58 41 51 - b 51 47 48 48 50 49 41 49 49 48 48 Ref.
255-260 196-198 190 148 182 - - 224 148 134 96 138 114 115 239 Ethyl acetate Ethyl acetatelight petroleum (b. p. 60-80") -b -b -b -b -b -b 62 62 65 65 58 61 61 62 62 62 62 62 63 58 58 58 58 Solvent of crystallization not specified. Colorless needles. Purified by sublimation. Yield not quoted. 6-Chloro derivative. 8-Chloro derivative. ' 6-Ethoxycarbonyl derivative. ' 8-Ethoxycarbonyl derivative. Hydrochloride. ' Buff needles. 5 hr); H = TiCI,, conc. HC1/(800)(1hr); I = conc. )(several hr); L = ZnCI,, Ac,O/(reflux)(3-4 hr).
Ring-closure Reactions of Other Heterocycles Substituent i n t e r a ~ t i o nin~ ~N-(orfho-substituted pheny1)pyrrolidines is a rich source of 2,3-dihydro- 1H-pyrrolo[1,2-a]benzimidazoles. 74)]. 8). 84)], since this transformation could be the result of deoxygenation followed by reductive cyclization (see later) of the N-(2-nitrophenyl)pyrrolidine produced. ” The acid-catalyzed cyclization of N-(2-benzamidophenyl)pyrrolidin-2-one is reporteds6 to afford 2,3-dihydro- 1H-pyrrolo[1,2-a]benzimidazole, albeit in unspecified yield.