| Autor: |
Rao RN; Department of Chemistry, School of Advanced Sciences, Vellore Institute of Technology, Vellore 632014, India. chandakaushik1@gmail.com., Das S; Department of Chemistry, School of Advanced Sciences, Vellore Institute of Technology, Vellore 632014, India. chandakaushik1@gmail.com., Jacob K; Department of Chemistry, School of Advanced Sciences, Vellore Institute of Technology, Vellore 632014, India. chandakaushik1@gmail.com., Alam MM; Department of Chemistry, College of Science, King Khalid University, P.O. Box 9004, Abha 61413, Saudi Arabia., Balamurali MM; Chemistry Division, School of Advanced Sciences, Vellore Institute of Technology, Chennai, Tamil Nadu, 600027, India. mmbala@gmail.com., Chanda K; Department of Chemistry, School of Advanced Sciences, Vellore Institute of Technology, Vellore 632014, India. chandakaushik1@gmail.com.; Department of Chemistry, Rabindranath Tagore University, Hojai 782435, Assam, India. |
| Abstrakt: |
A one-pot microwave assisted telescopic approach is reported for the chemo-selective synthesis of substituted 1,3-thiazetidines using readily available 2-aminopyridines/pyrazines/pyrimidine, substituted isothiocyanates and 1,2-dihalomethanes. The procedure involves thiourea formation from 2-aminopyridines/pyrazines/pyrimidine with the substituted isothiocyanates followed by a base catalysed nucleophilic attack of the CS bond on the 1,2-dihalomethane. Subsequently, a cyclization reaction occurs to yield substituted 1,3-thiazetidines. These four membered strained ring systems are reported to possess broad substrate scope with high functional group tolerance. The above synthetic sequence for the formation of four membered heterocycles is proven to be a modular and straightforward approach. Further the mechanistic pathway for the formation of 1,3-thiazetidines was supported by computational evaluations and X-ray crystallography analyses. The relevance of these thiazetidines in biological applications is evaluated by studying their ability to bind bio-macromolecules like proteins and nucleic acids. |
