Iminodiacetic acid derivatives of benzimidazole. Synthesis of N-(Benzimidazol-2-ylmethyl)iminodiacetic acids

Abstract

Ten new N-(2-benzimidazolylmethyl)iminodiacetic acids (BIMIDA)* have been synthesized from the corresponding o-phenylenediamines via intermediate 2-chloromethyl and 2-aminomethyl benzimid- azoles as ligands for 99mTc. Anomalies associated with the synthesis of the iodo-substituted compound are described.

Complexes of N-hydroxyethyl-N-benzimidazolylmethylethylenediaminediacetic acid with group 12 metals and vanadium—Synthesis, structure and bioactivity of the vanadium complex

“…Double distilled water was used to prepare the solutions. The ligand L was prepared according to the method of synthesis described in the literature [35] (elemental analysis calcd. C 54.85, H 6.33, N 15.99; found C 54.52, H 6.48, N 16.14).…”

Exploring the Strength of the H‐Bond in Synthetic Models for Heme Proteins: The Importance of the N−H Acidity of the Distal Base

“…Specifically, the preparation of 5‐iodo‐2‐methyl‐1 H ‐benzimidazole ( 13 ) was achieved in one step by the Na 2 S 2 O 4 reduction of 4‐iodo‐2‐nitroaniline ( 19 ) in the presence of acetaldehyde . Reduction of aniline 19 , followed by treatment with TFA in the presence of catalytic HCl, gave 5‐iodo‐2‐(trifluoromethyl)‐1 H ‐benzimidazole ( 14 ) in 62 % overall yield . 5‐Iodo‐1,3‐dihydro‐2 H ‐benzimidazol‐2‐one ( 12 ) was obtained by treatment of 4‐iodobenzene‐1,2‐diamine ( 20 ) with 1,1′‐carbonyldiimidazole .…”

“…The synthesis of precursor 18 was carried out in a similar manner (Scheme ). Specifically, 6‐iodo‐3‐nitropyridin‐2‐amine ( 26 ) was treated with SnCl 2 ⋅2H 2 O and 12 n HCl to afford 6‐iodopyridine‐2,3‐diamine ( 27 ) in 45 % yield. Subsequent cyclization of diamine 27 in the presence of formic acid gave 18 in 50 % yield.…”

“…Porphyrins 1‐Ζn and 10‐Ζn , benzimidazole 11 , 4‐iodo‐2‐nitroaniline ( 19 ), 3‐fluoro‐2‐nitroaniline ( 22 ), and 6‐iodo‐3‐nitropyridin‐2‐amine ( 26 ) were prepared according to known literature procedures. The Supporting Information (SI) contains: synthesis of porphyrin 10‐Ζn ; proposed mechanism for the formation of porphyrin 9‐Zn ; synthetic procedures and spectral data of zinc porphyrins 2 – 9‐Zn , free‐base porphyrins 1 – 9 – 2 H , cobalt porphyrins 1 – 9‐Co , iodinated distal base precursors 12 – 18 , and precursor compounds 19 – 27 ; copies of UV/Vis spectra, 1D and 2D NMR spectra of all new compounds; X‐band cw‐EPR and Q‐band Davies‐ENDOR spectra.…”

Assessing the impact of comorbid illnesses on death within 10 years in prostate cancer treatment candidates

“…The synthesis of N ‐octyl substituted 2,2′‐(1,4‐phenylene)‐bis(benzimidazole) ( 7 ) started with commercially available 2‐nitroaniline ( 1 ). To obtain compound 2 , it is essential to add less than 1 equiv of N ‐bromosuccinimide (NBS) to prevent the formation of dibromination products which are difficult to remove 38. Compound 5 was synthesized according to the previously reported approach 39.…”