Regioselective N-alkylation of benzimidazole via an organotin route

Soundararajan, R.; Balasubramanian, Thiagarajan

doi:10.1016/s0040-4039(01)81624-5

Cited by 10 publications

(1 citation statement)

References 6 publications

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“…2-Phenacylbenzimidazoles can be obtained by a variety of methods [5][6][7][8][9][10][11][12][13]. The aforementioned syntheses are characterized by low yield; therefore, 2-phenacylbenzimidazoles were prepared by treating methylbenzimidazole 1 with benzoyl chlorides in the presence of triethylamine followed by thermal decomposition of formed (Z)-2-(1-benzoyl-1H-benzo[d]imidazol-2-yl)-1-phenylvinyl benzoates 2a-i (Scheme 2) [5,7,11].…”

Section: Resultsmentioning

confidence: 99%

Tautomeric Equilibria in Solutions of 2-Phenacylbenzimidazoles

Skotnicka

Czeleń

Gawinecki

2019

Heteroatom Chemistry

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Detailed NMR spectral analysis of DMSO-d6 solutions of the series of substituted 2-phenacylbenzimidazoles (ketimine form, K) reveals two from three tautomeric forms. Integrals of the 1H NMR signals are used in establishing the molar ratio of tautomers. The experimental analyses are supported by quantum-chemical calculations, which satisfactorily reproduced the experimental trends. Although the reported semiempirical quantum-chemical calculations show that enaminone E, i.e., 2-(1,3-dihydro-2H-benzo[d]imidazol-2-ylidene)-1-phenylethan-1-one, was thermodynamically most stable, the results of MP2 ab initio calculations reveal the following order of stability: ketimine > enolimine > enaminone (substituents do not affect this sequence). 13C CPMAS NMR spectral data reveal that in the crystalline state the enolimine tautomer O is predominant in the p-CH3 and p-NO2 substituted congeners.

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Section: Resultsmentioning

confidence: 99%

Tautomeric Equilibria in Solutions of 2-Phenacylbenzimidazoles

Skotnicka

Czeleń

Gawinecki

2019

Heteroatom Chemistry

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ChemInform Abstract: REGIOSELECTIVE N‐ALKYLATION OF BENZIMIDAZOLE VIA AN ORGANOTIN ROUTE

Soundararajan¹,

Balasubramanian²

1985

Chemischer Informationsdienst

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Green and fast procedure to obtainN‐alkylbenzimidazole derivatives under microwave activation

Casilda

Martı́n-Aranda

López-Peinado

2010

Env Prog and Sustain Energy

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In this research, we report for the first time the one‐pot microwave‐assisted synthesis of N‐butylbenzimidazole derivatives via alkylation of benzimidazole with 1‐bromobutane over alkali‐metal doped carbons in absence of any solvent. N‐alkylbenzimidazole derivatives are produced in high yields and in very short reaction times when NaCs‐Norit is used as catalyst (ca. 75% in 5 min). Thus the combination of microwaves and basic carbons in dry media leads to the simplest, most eco‐efficient and fastest procedure reported so far for the preparation of benzimidazole derivatives with pharmacological properties. Under these mild reaction conditions, N‐butylbenzimidazoles are obtained with total selectivity to be used in many important industrial applications. © 2010 American Institute of Chemical Engineers Environ Prog, 2011

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Regioselective N-alkylation of benzimidazole via an organotin route

Cited by 10 publications

References 6 publications

Tautomeric Equilibria in Solutions of 2-Phenacylbenzimidazoles

Tautomeric Equilibria in Solutions of 2-Phenacylbenzimidazoles

ChemInform Abstract: REGIOSELECTIVE N‐ALKYLATION OF BENZIMIDAZOLE VIA AN ORGANOTIN ROUTE

Green and fast procedure to obtainN‐alkylbenzimidazole derivatives under microwave activation

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