Ionic Liquid Promoted Regio‐Selective Synthesis of 2‐Methyl amino‐3‐Nitro‐pyrano[3, 2‐c]chromen‐5‐ones. Issue 23 (14th June 2022)

• Record Type: Journal Article
• Authors: Katariya, Ashishkumar P.; Gaikwad, Pravinkumar B.; Kadam, Gajanan G.; Katariya, Maya V.; Deshmukh, Satish U.
• Is Part Of: ChemistrySelect. Volume 7:Issue 23(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-06-14
• Subjects: (E)-N-methyl-1-(methylthio)-2-nitroethenamine (NMSM) -- Functionalized pyrano[3, 2-c]chromen-5-ones -- Ionic liquid [(EMIM)Ac] -- Knoevenagel reaction -- Michael-addition reaction; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.202201295
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: An efficient, and simple protocol for the synthesis of extremely functionalized pyrano[3, 2‐ c ]chromen‐5‐ones (4 a–v ) has been developed. One‐pot multicomponent cyclo‐condensation of 4‐hydroxycoumarin, aromatic‐aldehydes, and ( E )‐N‐methyl‐1‐(methylthio)‐2‐nitroethenamine (NMSM) catalyzed by ionic liquid [(EMIM)Ac] in two different methods as methanolic mediated and at solvent free condition is described which presumably involve the Knoevenagel reaction succeeding Michael‐addition and O ‐cyclization with elimination of methanethiol. The noteworthy features of this protocol are use of ionic liquid as catalyst, good to excellent yield, optimum reaction time with easy experimental procedure. The prepared derivatives were characterized by IR, 1 HNMR, 13 CNMR and HRMS spectroscopic techniques. Abstract : An efficient, and simple protocol for the synthesis of extremely functionalized pyrano[3, 2‐ c ] chromen‐5‐ones (4 a–v) has been developed. One‐pot multicomponent cyclo‐condensation of 4‐hydroxycoumarin, aromatic‐aldehydes, and ( E )‐N‐methyl‐1‐(methylthio)‐2‐nitroethenamine (NMSM) catalyzed by ionic liquid [(EMIM)Ac] in two different methods as methanolic mediated and at solvent free condition is described which presumably involve the Knoevenagel reaction the succeeding Michael‐addition and O ‐cyclization with elimination of methanethiol. The noteworthy features of this protocol are use of ionic liquid as catalyst, good to excellent yield, optimum reaction time with easy experimental procedure. The prepared derivatives were characterized by IR, 1 HNMR, 13 CNMR and HRMS spectroscopic techniques.