Tandem Synthesis and Optical Rotatory Dispersion Studies of a Novel Spiro Lactone (methyl 3-(benzo[d]thiazol-2-ylamino)-7,9-dimethyl-2,6,8,10-tetraoxo-1-oxa-7,9-diazaspiro[4.5]dec-3-ene-4-carboxylate)

Subject Areas :

Karim Ghafouri ¹ , Samira Arab-salmanabadi ² , Sajjad Sedaghat ³

1 - Department of Chemistry, Shahr-e-Qods Branch, Islamic Azad University, Tehran , Iran
2 - Department of Chemistry, Shahr-e-Qods Branch, Islamic Azad University, Tehran , Iran
3 - Department of Chemistry, Shahr-e-Qods Branch, Islamic Azad University, Tehran , Iran

Received: 2017-04-09 Accepted : 2017-06-23 Published : 2017-09-01

Keywords: Alloxan, Spiro lactone, Tandem reaction, Benzo[d]thiazol-2-amine, Special optical rotatory,

Abstract :

Spiro compounds are of interest due to their interesting conformational features and their structural implications on biological systems. The asymmetric characteristic of the molecule due to the chiral spiro carbon is one of the important criteria of the biological activities. These structures are a widespread structural motif found as key elements of numerous drugs and designed medicinal agents in medicinal chemistry. Synthesis of these compounds always has been a challenging for organic chemists because it often requires synthetic design based on specific strategies. Due to the great importance of this class of compounds, chemists have a special attention to the synthesis of these compounds and a range of synthesis methods has been reported. In the current research a novel optically active spiro-lactone was synthesized via a tandem protocol ( michael addition, aldol reaction and γ-lactonization consecution) between benzo[d]thiazol-2-amine and dimethyl-acetylene dicarboxylate in the presence of 2, 4, 5, 6(1H, 3H)–pyrimidinetetrone (Alloxan). The synthesized compound has been successfully characterized by spectroscopy techniques. Also, evaluation of special optical rotatory on this synthesized spiro-lactone was investigated.