Industrial Consultancy & Sponsored Research (IC&SR) , IIT Madras
Cu-catalyzed Domino Synthesis of Thioaurone and Thioindirubin from Odorless Xanthate as Sulfur Surrogate
Technology Category/Market
Category –Chemistry & Chemical Analysis
Applications –Chemicals,Drugs and pharmaceuticals, manufacturing
Industry –Chemicals, Pharmaceuticals, Textiles
Market – Organic Chemicals Market Size was valued at USD 11.3 Billion in 2022 and is projected to grow from 12.15 Billion in 2023 to USD 21.66 Billion by 2032, exhibiting a compound annual growth rate (CAGR) of 7.50% during the said forecasting period
Image
Problem Statement
- Conventionally, thioindirubin derivatives are prepared by radical intramolecular cyclization of triethylammonium thiolates utilizing expensive starting materials
- Further, multistep process is required to prepare the starting material
Technology
- The present invention describes the copper iodide (VII) catalyzed synthesis of thioaurone (I) and thioindirubin (II) from the 2-iodochalcones (III, IV).
- Potassium ethyl xanthate (V)(sulfur source) used along with iodine as additive (VI) in 1,4-Dioxane (VIII) at reflux temperature of 120 oC.(Fig.1)
- The reaction proceeds via sulfur insertion and simultaneous region-selective cyclization Two C-S σ–bonds, one C-C σ-bond and one C=C π-bonds were formed in this single step.
- The same protocol is applied for attaining synthetically important several thioindirubin derivatives
- Period of the time may vary depends on the substitution of the starting materials all reactions are monitored by thin layer chromatography and the product is extracted , further purified by silica gel column chromatography
Key Features/Value Proposition
Technical Perspective
- Environmentally benign and cost-effective copper catalyst to perform the domino reaction that furnished thioaurone and thioindirubin derivatives in excellent yields with pure form
- The process resulted in (Z)-2-(4- methylbenzylidene) benzo[b]thiophen-3(2H)-one in 92% yield after 24h and(E)-1-benzyl-5-methyl-3-(3-oxobenzo[b]thiophen -2(3H)-ylldene) indolin-2-one in 83% yield after 28 h
User Perspective:
- Odourless, and avoids use of hazardous solvents and inert atmosphere to carry out the reaction.
- Easy handling of starting materials, air atmosphere, energy efficient process, applied in industrial scale
- Shows cytotoxicity to cancer cells and fat affinity, possess a wide range application, also used in dyes
Questions about this Technology?
Contact for Licensing
Research Lab
Prof. Govindasamy Sekar
Department of Chemistry
Intellectual Property
- IITM IDF Ref. 2218
- IN 402159-Granted
Technology Readiness Level
TRL-3
Experimental proof of concept