105259-40-3Relevant academic research and scientific papers
Novel N-ferrocenylmethyl, N′-methyl-2-substituted benzimidazolium iodide salts with in vitro activity against the P. falciparum malarial parasite strain NF54
Howarth, Joshua,Hanlon, Keith
, p. 751 - 754 (2001)
Herein we disclose results of our research into a novel class of benzimidazolium compounds active against malarial parasites. We have discovered that N-ferrocenylmethyl, N′-methyl-2-aryl (or styryl) benzimidazolium iodide salts show excellent in vitro activity against the P. falciparum malarial parasite strain NF54.
Enantioselective aza Michael-type addition to alkenyl benzimidazoles catalyzed by a chiral phosphoric acid
Wang, Ya-Yi,Kanomata, Kyohei,Korenaga, Toshinobu,Terada, Masahiro
, p. 927 - 931 (2016)
Highly enantioselective Michael-type addition (MTA) reactions between N-protected alkenyl benzimidazoles and either pyrazoles or indazoles as nitrogen nucleophiles are accomplished for the first time using chiral phosphoric acid catalyst. Theoretical studies elucidated the reaction pathway and the origin of the stereochemical outcomes, where the catalyst substituent and the N-protecting group of benzimidazole contributed to the resulting high enantioselectivity. Heterocycle squared: Highly enantioselective Michael-type addition reactions to alkenyl benzimidazoles with pyrazoles and indazoles as nitrogen nucleophiles are accomplished using a chiral phosphoric acid catalyst. Theoretical studies elucidated the reaction pathway and the origin of the stereochemical outcome. The catalyst substituent and the N-protecting group (PG) of the benzimidazole contribute to the resulting high enantioselectivity.
Reaction of imidazoles with allyltributyltin in the presence of chloroformate
Itoh, Takashi,Hasegawa, Hiroshi,Nagata, Kazuhiro,Okada, Mamiko,Ohsawa, Akio
, p. 5399 - 5402 (1992)
The reaction of imidazoles with allyltributyltin in the presence of chloroformate gave 2-allyl-1,3-dialkoxycarbonyl-4-imidazolines in good yields. The addition products were aromatized with potassium ferricyanide under basic condition to afford corresponding 2-allylimidazoles.
Weinreb amide as an efficient reagent in the one pot synthesis of benzimidazoles and benzothiazoles
Bommegowda, Yadaganahalli K.,Lingaraju, Gejjalagere S.,Thamas, Saji,Vinay Kumar, Koravangala S.,Pradeepa Kumara, Challanayakanahally S.,Rangappa, Kanchugarakoppal S.,Sadashiva, Marilinganadoddi P.
supporting information, p. 2693 - 2695 (2013/06/05)
One pot synthesis of 2-substituted benzimidazoles/benzothiazoles through condensation is followed by cyclization of Weinreb amide with o-diaminoarene or o-aminothiophenol is reported. In the presence of boron trifluoride etherate in 1,4-dioxane solvent, a high yield (75-94%) was achieved within 60 min. Weinreb amide shows high selectivity in the reaction, even in presence of other active functional groups such as carboxyl, halogen, cyano, and methoxy.
Allylation of Azoles with Allyltributyltin via Unstable N-(Alkoxycarbonyl)azolium Salts
Itoh, Takashi,Hasegawa, Hiroshi,Nagata, Kazuhiro,Ohsawa, Akio
, p. 1319 - 1325 (2007/10/02)
The one-pot reactions of imidazoles with allyltributyltin in the presence of alkyl chloroformates gave 2-allyl-1,3-bis(alkoxycarbonyl)-4-imidazolines in good yields.The reactions of thiazoles and oxazoles also proceeded in a similar manner.The instability of the intermediary quaternary salts required the nucleophiles to be added simultaneously with the chloroformate.Therefore, the reaction was specific for allyltributyltin, since it doesn't react with the carbonyl group of chloroformates.The dihydro allyl adducts thus obtained were aromatized with potassium ferricyanide under basic conditions to afford the corresponding 2-allylazoles.
