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

Andrejs Krasikovs; Vita Ozola; Scott L. Dax; Edgars Suna

doi:10.1055/s-0032-1316849

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(5): 683-693
DOI: 10.1055/s-0032-1316849

paper

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

Andrejs Krasikovs

^aLatvian Institute of Organic Synthesis, Aizkraukles 21, 1006 Riga, Latvia Fax: +371(6)7550338 eMail: edgars@osi.lv

,

Vita Ozola

^aLatvian Institute of Organic Synthesis, Aizkraukles 21, 1006 Riga, Latvia Fax: +371(6)7550338 eMail: edgars@osi.lv

,

Scott L. Dax

^bGalleon Pharmaceuticals, 213 Witmer Road, Horsham, PA 19044, USA

,

Edgars Suna*

^aLatvian Institute of Organic Synthesis, Aizkraukles 21, 1006 Riga, Latvia Fax: +371(6)7550338 eMail: edgars@osi.lv

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Abstract

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Abstract

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.

Key words

amino acids - cyclization - desulfurization - green chemistry - heterocycles

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Referenzen

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