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Benzimidazoles and Cogeneric Tricyclic Compounds, Part 2 by P. N. Preston

By P. N. Preston

The Chemistry of Heterocyclic Compounds, due to the fact its inception, has been famous as a cornerstone of heterocyclic chemistry. each one quantity makes an attempt to debate all facets – houses, synthesis, reactions, physiological and commercial value – of a selected ring procedure. to maintain the sequence updated, supplementary volumes protecting the new literature on each one person ring approach were released. Many ring platforms (such as pyridines and oxazoles) are taken care of in distinctive books, every one including separate volumes or components facing diversified person issues. With all authors are famous gurus, the Chemistry of Heterocyclic Chemistry is taken into account around the globe because the fundamental source for natural, bioorganic, and medicinal chemists.

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Extra resources for Benzimidazoles and Cogeneric Tricyclic Compounds, Part 2 (The Chemistry of Heterocyclic Compounds, Volume 40)

Example text

96) by the solvent. 91) in ethanolic hydrochloric acid can likewise be r a t i o n a l i ~ e d in ~ . terms ~ ~ of initial anil formation followed by cyclization to and in situ oxidation of a tetrahydro- 1H-pyrrolo[1,2-a]benzimidazole intermediate [cf. 97)]. 9). 88)p9provide evidence for the intermediacy of 2,3,3a,4-tetrahydro-l H-pyrrolo[ 1,2-a]benzimidazoles in the presumed nitrene-initiated cyclizations of N-(2-azidophenyl)pyrroIidines leading to 2,3-dihydro- 1H-pyrrolo[ 1,2-a]benzimidazole derivatives (see before).

78; R' = H, R2= NO,, 61 33 67 68 70 13 32 16 78 quant. quant. ) 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.

7). 54; R' = R3= R4= H, R2 = Me) stands in contrast to the isomer mixture obtained3' (cf. 57; R' = R5 = Me, R2 = R3 = R4 = H). This latter result casts some doubt on the specificity of the cyclization of electronically biased 5(6)-substituted benzimidazoles by preferential ring-closure at the nitrogen atom para to the substituent. p. 1. 70)]. 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.

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