Iodoacetic Acid is an Efficient Reagent for the Synthesis of Amino Acid Derived 2-Aminobenzimidazoles

Synthesis 2013
A. Krasikovs, V. Ozola, S.L. Dax, Edgars Sūna

Chiral, nonracemic, N-unprotected amino acids were converted into the corresponding N-benzimidazol-2-yl derivatives by a sequential procedure involving initial formation of isothiocyanates, their reaction with arene-1,2-diamines, and cyclization-desulfurization of the intermediate thioureas with iodoacetic acid. The simplified workup and the lack of volatile or toxic byproducts in the key desulfurization step renders iodoacetic acid a superior reagent to the usual reagent, iodomethane.

Keywords
amino acids - cyclization - desulfurization - green chemistry - heterocycles
DOI
10.1055/s-0032-1316849
Hyperlink
https://www.thieme-connect.de/DOI/DOI?10.1055/s-0032-1316849

Krasikovs, A., Ozola, V., Dax, S., Sūna, E. Iodoacetic Acid is an Efficient Reagent for the Synthesis of Amino Acid Derived 2-Aminobenzimidazoles. Synthesis, 2013, Vol.45, Iss.23, pp.683-693. e-ISSN 1437-210X. ISSN 0039-7881. Available from: doi:10.1055/s-0032-1316849

Publication language
English (en)