title: Tandem aldehyde-alkyne-amine coupling/cycloisomerization: A new synthesis of coumarins.
abstract: Cu-catalyzed A(3) coupling of ethoxyacetylene, pyrrolidine and salicylaldehydes led to a concomitant cycloisomerization followed by hydrolysis of the resultant vinyl ether to afford coumarins in a cascade process. The reaction proceeded through exclusive 6-endo-dig cyclization and is compatible with halo and keto groups giving coumarins in good to moderate yields.
authors: Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow-226 001, India, , Tel: +91-(522)-2612 411, Extn: 4379.
authors: Maddi Sridhar
authors: MS
authors: Reddy
authors: Nuligonda
authors: N
authors: Thirupathi
authors: Madala
authors: M
authors: Haribabu
keywords: A coupling; cooperative catalysis; coumarin synthesis; cycloisomerization; transition-metal catalysts
references: J Org Chem. 2010 Feb 5;75(3):897-901
references: 20043652
references: J Org Chem. 2008 Jul 4;73(13):4971-7
references: 18540650
references: J Org Chem. 2011 Jun 17;76(12):4995-5005
references: 21524121
references: J Med Chem. 2007 Nov 29;50(24):6189-200
references: 17979263
references: Bioorg Med Chem Lett. 2008 Apr 1;18(7):2495-8
references: 18304811
references: J Org Chem. 2011 Mar 4;76(5):1269-84
references: 21268618
references: Org Biomol Chem. 2012 Apr 7;10(13):2692-8
references: 22354061
references: Org Lett. 2007 Oct 11;9(21):4323-6
references: 17854200
references: Chem Soc Rev. 2012 May 21;41(10):3790-807
references: 22422343
references: Org Lett. 2011 Oct 7;13(19):5112-5
references: 21916521
references: Phytother Res. 2010 Jan;24(1):101-6
references: 19468986
references: Org Lett. 2008 Dec 18;10(24):5513-6
references: 19053726
references: Chem Commun (Camb). 2011 May 28;47(20):5879-81
references: 21499639
references: J Am Chem Soc. 2003 Apr 16;125(15):4518-26
references: 12683822
references: Adv Synth Catal. 2010 Apr 19;352(6):961-966
references: 23620715
references: Planta Med. 2003 Nov;69(11):1048-51
references: 14735445
references: J Org Chem. 2009 Sep 18;74(18):7052-8
references: 19673483
references: Org Lett. 2011 Jun 17;13(12):3178-81
references: 21604735
references: J Org Chem. 2002 Dec 27;67(26):9449-51
references: 12492352
references: Curr Med Chem Anticancer Agents. 2005 Jan;5(1):29-46
references: 15720259
references: Angew Chem Int Ed Engl. 2007;46(13):2295-8
references: 17300118
references: Org Lett. 2012 May 18;14(10):2520-3
references: 22545702
references: Org Lett. 2012 Feb 3;14(3):824-7
references: 22276912
references: Org Biomol Chem. 2011 Jun 21;9(12):4405-16
references: 21487625
references: J Org Chem. 2010 Feb 19;75(4):1266-70
references: 20099928
references: J Am Chem Soc. 2010 Jun 2;132(21):7256-7
references: 20455531
references: Nat Prod Rep. 1997 Oct;14(5):465-75
references: 9364778
references: Org Lett. 2009 Jan 1;11(1):173-6
references: 19046068
references: Org Lett. 2010 Oct 1;12(19):4420-3
references: 20828120
references: J Org Chem. 2012 Jul 20;77(14):6179-85
references: 22780441
references: Angew Chem Int Ed Engl. 2010 Apr 1;49(15):2743-6
references: 20213787
references: Med Res Rev. 2008 Jan;28(1):118-54
references: 17979144
references: J Org Chem. 2010 Feb 19;75(4):1277-80
references: 20092269
references: J Org Chem. 2000 Nov 3;65(22):7516-22
references: 11076610
references: J Org Chem. 2010 Oct 15;75(20):6961-4
references: 20857944
references: J Am Chem Soc. 2008 Nov 19;130(46):15720-5
references: 18942781
references: Chemistry. 2012 May 14;18(20):6133-7
references: 22511531
references: Org Lett. 2012 May 18;14(10):2622-5
references: 22564029
references: J Org Chem. 2011 Oct 7;76(19):7633-40
references: 21744859
references: J Am Chem Soc. 2011 Dec 14;133(49):19630-3
references: 22066605
references: Org Biomol Chem. 2010 Feb 7;8(3):511-21
references: 20090963
references: Org Lett. 2006 Jan 19;8(2):243-6
references: 16408885
references: J Biol Chem. 2000 Nov 24;275(47):37181-6
references: 10945979