Water extract of onion catalyst: An economical green route for the synthesis of 2‐substituted and 1,2‐disubstituted benzimidazole derivatives with high selectivity.

Autor: Kaliyan, Prabakaran, Selvaraj, Loganathan, Muthu, Seenivasa Perumal
Předmět:
Zdroj: Journal of Heterocyclic Chemistry; Jan2021, Vol. 58 Issue 1, p340-349, 10p
Abstrakt: An efficient, environmental friendly and substrate controlled method of synthesis of 2‐substituted benzimidazole derivatives 3 and 1,2‐disubstituted benzimidazole derivatives 4 with high selectivity has been achieved from the reaction of o‐phenylenediamine 1 and aldehydes 2 in the presence of water extract of onion and selecting suitable reaction medium. This method is widely applicable for variety of aldehydes such as aromatic/aliphatic/heterocyclic aldehydes and 1,2‐diamines to afford 2‐substituted benzimidazole derivatives 3 and 1,2‐disubstituted benzimidazole derivatives 4 in good to excellent yields (up to 96%). The developed method of water extract of onion catalysis produced 2‐substituted benzimidazoles 3 from aromatic aldehydes having electron‐withdrawing groups, whereas aromatic aldehydes bearing electron donating groups selectively furnished 1,2‐disubstituted benzimidazole 4 derivatives. The process described here has several advantages of cheap, low energy consumption, commercially available starting materials, operational simplicity and nontoxic catalyst. The use of water extract of onion makes this present methodology green and giving a useful contribution to the existing methods available for the preparation of benzimidazole derivatives. In addition, Hammett correlation of substituent constant (σ) vs percentage (%) yield has been established. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index
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