By P. N. Preston
The Chemistry of Heterocyclic Compounds, due to the fact its inception, has been well-known as a cornerstone of heterocyclic chemistry. each one quantity makes an attempt to debate all features – houses, synthesis, reactions, physiological and business value – of a particular ring method. to maintain the sequence up to date, supplementary volumes masking the hot literature on each one person ring procedure were released. Many ring platforms (such as pyridines and oxazoles) are handled in distinctive books, each one including separate volumes or elements facing assorted person subject matters. With all authors are well-known professionals, the Chemistry of Heterocyclic Chemistry is taken into account around the globe because the imperative 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)
Sample text
24). General Studies The typically basic character of 3H and 4H-pyrrolo[1,2-a]benzimidazoles, 2,3-dihydro-lH-pyrrolo[1,2-aJbenzimidazoles, and 2,3,3a,4-tetrahydro- lH-pyrrolo[l,2-a Jbenzimidazoles is qualitatively demons~ated12. , hydrochlorides, perchlorates, and picrates, cf. 9). Surprisingly, however, only a few quantitative of the basicity of pyrrolo[1,2-a]benzimidazoles of the various structural types appear to have been carried out.
It is conceivable that, as in the case of other acid-catalyzed aromatic nitro group ortho side-chain interactions,& cyclization is the end result of direct aldol-type condensation between the nitro group and an a-methylene center in the pyrrolidine ring activated by protonation of the adjacent nitrogen atom. 8). Isolated instances of ring-closure reactions leading to 2,3-dihydro- 1Hpyrrolo[ 1,2-a]benzimidazoles include the transformation (Scheme 6. 1. %)]. 94; R = 2-CI. ) 68 68 68 68 68 J J --I -I J J 1 ' 68 68 68 68 68 68 68 68 68 68 68 68 68 68 68 Ref.
108)] ester and ketonic substituents at the C(1) and C(3) positions in 4H-pyrrolo[ 1,2-a]benzimidazoles absorb at significantly lower frequencies (cf. 10) than their C(2) counterparts. 102) with the other nitrogen center and the benzene ring. 103). The IR spectra" of simple 3H-pyrrolo[ 172-a]benzimidazoles contain characteristic bands at 1630-1625 cm-'. 111), not unexpectedly in view of the saturated nature of the fused five-membered ring present, resemble that of 1methylbenzimidazole. 92)] is akin to that of the benzimidazolium cation.
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