78078-13-4Relevant academic research and scientific papers
One-Pot Mitsunobu Protocol to Access Ketene S,S-/N,S-Acetals at Room Temperature
Saha, Priya,Ansari, Monish Arbaz,Shukla, Gaurav,Singh, Maya Shankar
supporting information, p. 5884 - 5888 (2021/11/27)
With unique chemical reactivity, α-oxoketene S,S- and N,S-acetals have attracted enormous attention in the past decades, whereas limited reports exist for their synthesis via eco-compatible protocols. Herein, we developed a one-pot protocol for symmetrical and unsymmetrical α-oxoketene S,S-/N,S-acetals through chemoselective alkylation of α-enolic dithioesters using Mitsunobu chemistry at room temperature. The operationally simple and user-friendly mild protocol tolerates a wide range of alcohols and α-enolic dithioesters/β-ketothioamides. Short reaction time, good yields, highly selective C?S functionalization, and E/Z-stereoselectivity are imperative characteristics of this strategy.
ZnCl2-Catalyzed [4+1] Annulation of Alkylthio-Substituted Enaminones and Enaminothiones with Sulfur Ylides
He, Yuan,Lou, Jiang,Zhou, Yong-Gui,Yu, Zhengkun
supporting information, p. 4941 - 4946 (2020/03/30)
Concise construction of furan and thiophene units has played an important role in the synthesis of potentially bioactive compounds and functional materials. Herein, an efficient Lewis acid ZnCl2 catalyzed [4+1] annulation of alkylthio-substituted enaminones is reported, that is, α-oxo ketene N,S-acetals with sulfur ylides to afford 2-acyl-3-aminofuran derivatives. In a similar fashion, [4+1] annulation of the corresponding enaminothiones, that is, α-thioxo ketene N,S-acetals, with sulfur ylides efficiently proceeded to give multisubstituted 3-aminothiophenes. This method features wide substrate scopes as well as broad functional group tolerance, offering a concise route to highly functionalized furans and thiophenes.
A Highly Efficient Approach for the Synthesis of Novel Trifluoroacetylated Enaminones using DBU as a Base
Kumari,Sharma,Kumar,Mohapatra,Bhagat
supporting information, p. 2008 - 2013 (2017/09/13)
An efficient methodology has been developed for the synthesis of a variety of novel trifluoroacetylated enaminones by using trifluoroacetic anhydride in DCE as solvent and DBU as a base via electrophilic trifluoroacetylation. X-ray crystallographic studie
Synthesis of Novel Fluorinated Multisubstituted Pyrimidines and 1,5-Benzodiazepines via Fluorinated N,S-Acetals
Sharma, Nutan,Chundawat, Tejpal Singh,Mohapatra, Subash Chandra,Bhagat, Sunita
, p. 4495 - 4508 (2016/12/14)
An efficient and novel approach using highly versatile but less exploited monofluorinated α-oxoketene N,S-acetals as synthons for the synthesis of novel fluorinated multisubstituted pyrimidines and 1,5-benzodiazepines by cyclization with guanidine nitrate
DABCO-Promoted three-component regioselective synthesis of functionalized chromen-5-ones and pyrano[3,2-c]chromen-5-ones via direct annulation of α-oxoketene-N,S-arylaminoacetals under solvent-free conditions
Singh, Maya Shankar,Nandi, Ganesh Chandra,Samai, Subhasis
scheme or table, p. 447 - 455 (2012/03/26)
An efficient and convergent route to 3-aroyl-4-aryl-2-arylamino-4,6,7,8- tetrahydrochromen-5-ones and hitherto unreported 3-aroyl-4-aryl-2-arylamino-4H- pyrano[3,2-c]chromen-5-ones has been developed by an one-pot three-component domino coupling of α-oxok
Reaction of α-oxoketene dithioacetals with arylamines in the presence of BF3-OEt2 for the synthesis of ketene S,N-acetals
Kohra,Turuya,Kimura,Ogata,Tominaga
, p. 1293 - 1296 (2007/10/02)
Reaction of α-oxoketene dithioacetals with arylamines was accelerated with a catalytic amount of BF3-OEt2 to give the corresponding α-oxoketene S,N-acetals selectively in good yields.
