efficient one-pot synthesis of indol-3-yl-glycines via uncatalyzed friedel-crafts reaction in water高效合成indol-3-yl-glycines通过uncatalyzed傅克反应在水里.pdfVIP

Molecules 2009, 14, 1056-1061; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Efficient One-Pot Synthesis of Indol-3-yl-Glycines via Uncatalyzed Friedel-Crafts Reaction in Water Mehdi Ghandi * and Abuzar Taheri School of Chemistry, University College of Science, University of Tehran, Tehran, Iran * Author to whom correspondence should be addressed; E-mail: ghandi@khayam.ut.ac.ir; Tel.: +98- 21 Fax: +98-21 Received: 11 February 2009; in revised form: 25 February 2009 / Accepted: 3 March 2009 / Published: 5 March 2009 Abstract: The three component reaction of primary aliphatic amines, glyoxalic acid and indole or N-methylindole in water at ambient temperature affords indol-3-yl or N- methylindol-3-yl-glycine in almost quantitative yields. Keywords: Amino acid; Indol-3-yl-glycine; Glyoxalic acid; Friedel-Crafts reaction. Introduction The use of water as an environmentally benign solvent for organic synthesis has become an important research area from both the economical and synthetic point of view. The indole ring system is probably the most ubiquitous heterocycle in Nature [1]. Substituted indoles have been referred to as “privileged structures” since they are able to bind with high affinity to many receptors [2]. Indol-3-yl- glycine derivatives are one of the important non-proteinogenic amino acids for the synthesis of many biologically active compounds such as dragmacdins, hamacanthin and pemedolac [3-7]. Therefore, the development of new strategies