Multicomponent Reaction for Selective Synthesis of Spiro[indene‐2, 7′‐isoquinoline] and 1, 2, 8, 8 a‐Tetrahydroisoquinoline Derivatives. Issue 9 (4th March 2019)

• Record Type: Journal Article
• Authors: Cao, Jun; Sun, Jing; Yan, Chao‐Guo
• Is Part Of: ChemistrySelect. Volume 4:Issue 9(2019)
• Page Start: 2663
• Page End: 2667
• Publication Date: 2019-03-04
• Subjects: 1, 3-indanedione -- multicomponent reaction -- piperidin-4-one -- spiro[indene-2, 7′-isoquinoline] -- tetrahydroisoquinoline; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201803715
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: The piperidine promoted three‐component reaction of N ‐alkylpiperidin‐4‐ones, malononitrile and 2‐arylidene‐1, 3‐indanediones in ethanol selectively resulted in the spiro[indene‐2, 7′‐isoquinoline] and the ring‐opened cis ‐ or trans ‐1, 2, 8, 8 a ‐tetrahydroisoquinoline derivatives at room temperature or at the elevated temperature. However, the four‐component reaction N ‐alkylpiperidin‐4‐ones, malononitrile, aromatic aldehydes and 1, 3‐indanedione in refluxing ethanol mainly afforded ring‐opened cis ‐1, 2, 8, 8 a ‐tetrahydroisoquinoline derivatives in good yields and with high diastereoselectivity. A plausible domino reaction mechanism was proposed for the formation of the different polycyclic products. Abstract : The piperidine promoted three‐component reaction of N ‐alkylpiperidin‐4‐ones, malononitrile and 2‐arylidene‐1, 3‐indanediones in ethanol selectively resulted in the spiro[indene‐2, 7′‐isoquinoline] and the ring‐opened cis ‐ or trans ‐1, 2, 8, 8 a ‐tetrahydroisoquinoline derivatives at room temperature or at the elevated temperature. However, the four‐component reaction N ‐alkylpiperidin‐4‐ones, malononitrile, aromatic aldehydes and 1, 3‐indanedione in refluxing ethanol mainly afforded ring‐opened cis ‐1, 2, 8, 8 a ‐tetrahydroisoquinoline derivatives in good yields and with high diastereoselectivity.