A synthesis of (arylthio-ethylidene)indolin-2-ones via S-arylation of oxoindolin-ethanethiolates with aryl halides. (4th March 2019)

• Record Type: Journal Article
• Authors: Yavari, Issa; Taheri, Zohreh; Sheikhi, Sara; Halvagar, Mohammad Reza
• Is Part Of: Journal of sulfur chemistry. Volume 40:Number 2(2019)
• Page Start: 124
• Page End: 136
• Publication Date: 2019-03-04
• Subjects: S-Arylation -- Cu(I) iodide -- aryl halides -- 1-aryl-2-thiocyanatoethan-1-ones -- isatin; Sulfur -- Periodicals; Chemistry, Inorganic -- Periodicals; 546.72305
• DOI: 10.1080/17415993.2018.1540701
• Languages: English
• ISSNs: 1741-5993

Abstract

ABSTRACT: Aryl-sulfur bond formation between aryl halides and 1-(2-oxoindolin-3-ylidene)-2-aroylethanethiolates, prepared from isatin, 1-aryl-2-thiocyanatoethan-1-ones, and aryl halides, catalyzed by copper(I) iodide in DMF at 80°C afforded a nearly 1:1 mixture of ( Z/E )-3-(2-oxo-2-aryl-1-(arylthio)ethylidene)indolin-2-ones, in good yields. The stereochemistry of these products has been confirmed by X-ray diffraction studies. GRAPHICAL ABSTRACT: