Title:
Cu-MEDIATED ANNULATION FOR THE EFFECTIVE SYNTHESIS OF 3-SUBSTITUTED PHTHALIDES
Document Type and Number:
WIPO Patent Application WO/2013/102935
Kind Code:
A3
Abstract:
The present invention disclosed herein is a novel commercially feasible, one pot synthesis of library of 3-substituted phthalides of formula I via CuCN mediated oxidative cyclization in high yield. Formula I
Inventors:
REDDY SANTHOSH REKULA (IN)
PRAGATI KISHORE PRASAD (IN)
NAGA KIRAN CHAITHANYA INDUKURU (IN)
SUDALAI ARUMUGAM (IN)
PRAGATI KISHORE PRASAD (IN)
NAGA KIRAN CHAITHANYA INDUKURU (IN)
SUDALAI ARUMUGAM (IN)
Application Number:
PCT/IN2013/000005
Publication Date:
October 03, 2013
Filing Date:
January 03, 2013
Export Citation:
Assignee:
COUNCIL SCIENT IND RES (IN)
International Classes:
C07D307/88
Domestic Patent References:
| WO2010129379A1 | 2010-11-11 |
Other References:
DIEM H. T. PHAN ET AL: "Phthalides by Rhodium-Catalyzed Ketone Hydroacylation", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 131, no. 43, 4 November 2009 (2009-11-04), pages 15608 - 15609, XP055055590, ISSN: 0002-7863, DOI: 10.1021/ja907711a
KAZUHIRO KOBAYASHI ET AL: "An Efficient Synthesis of 3-Substituted 3H-Isobenzofuran-1-ylidenamines by the Reaction of 2-Cyanobenzaldehydes with Organolithiums and Their Conversion into Isobenzofuran-1(3H)-ones", HETEROCYCLES.INTERNATIONAL JOURNAL FOR REVIEWS AND COMMUNICATIONS IN HETEROCYCLIC CHEMISTRY, ELSEVIER SCIENCE PUBLISHERS B.V. AMSTERDAM, NL, vol. 83, no. 1, 1 January 2011 (2011-01-01), pages 99 - 106, XP009167763, ISSN: 0385-5414, DOI: 10.3987/COM-10-12071
GUANGLEI LV ET AL: "Rhodium or palladium-catalyzed cascade aryl addition/intramolecular lactonization of phthalaldehydonitrile to access 3-aryl and 3-alkenyl phthalides", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 67, no. 26, 29 April 2011 (2011-04-29), pages 4879 - 4886, XP028227655, ISSN: 0040-4020, [retrieved on 20110506], DOI: 10.1016/J.TET.2011.04.100
FOA M ET AL: "Cobalt-catalysed carbonylation of aryl halides", JOURNAL OF ORGANOMETALLIC CHEMISTRY, ELSEVIER-SEQUOIA S.A. LAUSANNE, CH, vol. 285, no. 1-3, 16 April 1985 (1985-04-16), pages 293 - 303, XP026619794, ISSN: 0022-328X, [retrieved on 19850416], DOI: 10.1016/0022-328X(85)87375-7
KATIE A. KEATON ET AL: "A Cyclopropanol-Based Strategy for Subunit Coupling: Total Synthesis of (+)-Spirolaxine Methyl Ether", ORGANIC LETTERS, vol. 9, no. 14, 1 July 2007 (2007-07-01), pages 2717 - 2719, XP055055790, ISSN: 1523-7060, DOI: 10.1021/ol0710111
HUA-MING MIAO ET AL: "Exquisite Synthesis of a Designed PAR-1 Antagonist", HELVETICA CHIMICA ACTA, vol. 94, no. 11, 1 November 2011 (2011-11-01), pages 1981 - 1993, XP055055516, ISSN: 0018-019X, DOI: 10.1002/hlca.201100128
S. ATTALURI ET AL: "DNA adducts of aristolochic acid II: total synthesis and site-specific mutagenesis studies in mammalian cells", NUCLEIC ACIDS RESEARCH, vol. 38, no. 1, 1 January 2010 (2010-01-01), pages 339 - 352, XP055055519, ISSN: 0305-1048, DOI: 10.1093/nar/gkp815
XIANG-HUI TAN ET AL: "Novel carbonyl allylation mediated by SnCl2/Cu in water", TETRAHEDRON LETTERS, vol. 43, no. 51, 1 December 2002 (2002-12-01), pages 9373 - 9376, XP055055807, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(02)02370-5
KOZO SHISHIDO ET AL: "An efficient total synthesis of ( )-decaline and ( )-vertaline", TETRAHEDRON LETTERS, vol. 24, no. 27, 1 January 1983 (1983-01-01), pages 2783 - 2786, XP055055798, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(00)88022-3
JACOPO ZANON ET AL: "Copper-Catalyzed Domino Halide Exchange-Cyanation of Aryl Bromides", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 125, no. 10, 1 March 2003 (2003-03-01), pages 2890 - 2891, XP055055809, ISSN: 0002-7863, DOI: 10.1021/ja0299708
KAZUHIRO KOBAYASHI ET AL: "An Efficient Synthesis of 3-Substituted 3H-Isobenzofuran-1-ylidenamines by the Reaction of 2-Cyanobenzaldehydes with Organolithiums and Their Conversion into Isobenzofuran-1(3H)-ones", HETEROCYCLES.INTERNATIONAL JOURNAL FOR REVIEWS AND COMMUNICATIONS IN HETEROCYCLIC CHEMISTRY, ELSEVIER SCIENCE PUBLISHERS B.V. AMSTERDAM, NL, vol. 83, no. 1, 1 January 2011 (2011-01-01), pages 99 - 106, XP009167763, ISSN: 0385-5414, DOI: 10.3987/COM-10-12071
GUANGLEI LV ET AL: "Rhodium or palladium-catalyzed cascade aryl addition/intramolecular lactonization of phthalaldehydonitrile to access 3-aryl and 3-alkenyl phthalides", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 67, no. 26, 29 April 2011 (2011-04-29), pages 4879 - 4886, XP028227655, ISSN: 0040-4020, [retrieved on 20110506], DOI: 10.1016/J.TET.2011.04.100
FOA M ET AL: "Cobalt-catalysed carbonylation of aryl halides", JOURNAL OF ORGANOMETALLIC CHEMISTRY, ELSEVIER-SEQUOIA S.A. LAUSANNE, CH, vol. 285, no. 1-3, 16 April 1985 (1985-04-16), pages 293 - 303, XP026619794, ISSN: 0022-328X, [retrieved on 19850416], DOI: 10.1016/0022-328X(85)87375-7
KATIE A. KEATON ET AL: "A Cyclopropanol-Based Strategy for Subunit Coupling: Total Synthesis of (+)-Spirolaxine Methyl Ether", ORGANIC LETTERS, vol. 9, no. 14, 1 July 2007 (2007-07-01), pages 2717 - 2719, XP055055790, ISSN: 1523-7060, DOI: 10.1021/ol0710111
HUA-MING MIAO ET AL: "Exquisite Synthesis of a Designed PAR-1 Antagonist", HELVETICA CHIMICA ACTA, vol. 94, no. 11, 1 November 2011 (2011-11-01), pages 1981 - 1993, XP055055516, ISSN: 0018-019X, DOI: 10.1002/hlca.201100128
S. ATTALURI ET AL: "DNA adducts of aristolochic acid II: total synthesis and site-specific mutagenesis studies in mammalian cells", NUCLEIC ACIDS RESEARCH, vol. 38, no. 1, 1 January 2010 (2010-01-01), pages 339 - 352, XP055055519, ISSN: 0305-1048, DOI: 10.1093/nar/gkp815
XIANG-HUI TAN ET AL: "Novel carbonyl allylation mediated by SnCl2/Cu in water", TETRAHEDRON LETTERS, vol. 43, no. 51, 1 December 2002 (2002-12-01), pages 9373 - 9376, XP055055807, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(02)02370-5
KOZO SHISHIDO ET AL: "An efficient total synthesis of ( )-decaline and ( )-vertaline", TETRAHEDRON LETTERS, vol. 24, no. 27, 1 January 1983 (1983-01-01), pages 2783 - 2786, XP055055798, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(00)88022-3
JACOPO ZANON ET AL: "Copper-Catalyzed Domino Halide Exchange-Cyanation of Aryl Bromides", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 125, no. 10, 1 March 2003 (2003-03-01), pages 2890 - 2891, XP055055809, ISSN: 0002-7863, DOI: 10.1021/ja0299708
Attorney, Agent or Firm:
CHOPRA, Priyanka et al. (Intellectual Property Attorneys109, Sector 4, Gurgaon National Capital Region 3, IN)
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