Synthesis of New 1-Substituted-1H-1,2,3,4-Tetrazoles from L-α-Amino Acids and Their Biological Assays

Author(s): Davood Habibi, Payam Rahmani, Fatemeh Ahmadi, Hanieh Bokharaei, Zahra Kaboudvand

Journal Name: Letters in Organic Chemistry

Volume 11 , Issue 2 , 2014


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Abstract:

A new series of 1-substituted 1H-1,2,3,4-tetrazoles was synthesized from the reaction of L-α-amino acids, triethylorthoformate and sodium azide in glacial acetic acid at 80 °C in good yields (55-80 %). Not only acetic acid is a good solvent but also an effective catalyst promoting the reaction compared with the Lewis acids/microwave, Lewis acids/ ultrasonic or Lewis acids/solvent-free conditions to give the corresponding 1H-1,2,3,4-tetrazoles. Also, the antimicrobial activity investigations (antibacterial activity against E. coli and antifungal activity against Candida albicans) showed that all the tetrazoles obtained were inactive except the one obtained from tryptophan. In addition, the obtained 1- substituted 1H-1,2,3,4-tetrazoles were resistant in different reducing and oxidizing conditions.

Keywords: L-α-Amino acids, sodium azide, 1H-1, 2, 3, 4-tetrazoles, triethylorthoformate, glacial acetic acid, antimicrobial activity.

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Article Details

VOLUME: 11
ISSUE: 2
Year: 2014
Published on: 20 January, 2014
Page: [145 - 151]
Pages: 7
DOI: 10.2174/15701786113106660072
Price: $65

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