Title:
PRODUCTION OF BENZENE DERIVATIVES
Document Type and Number:
WIPO Patent Application WO/2021/114207
Kind Code:
A1
Abstract:
A method of producing benzene derivatives from furfural and its derivatives. Provided are routes for converting furfural and its derivatives into benzene derivatives including its intermediates.
Inventors:
SCODELLER YVAN (IT)
JEROME FRANCOIS (FR)
DE OLIVEIRA VIGIER KARINE (FR)
MA CHANGRU (CN)
WISCHERT RAPHAEL (CN)
MULLER ERIC (FR)
JEROME FRANCOIS (FR)
DE OLIVEIRA VIGIER KARINE (FR)
MA CHANGRU (CN)
WISCHERT RAPHAEL (CN)
MULLER ERIC (FR)
Application Number:
PCT/CN2019/125046
Publication Date:
June 17, 2021
Filing Date:
December 13, 2019
Export Citation:
Assignee:
RHODIA OPERATIONS (FR)
CENTRE NAT RECH SCIENT (FR)
UNIV POITIERS (FR)
CENTRE NAT RECH SCIENT (FR)
UNIV POITIERS (FR)
International Classes:
C07C69/75; C07C2/50
Domestic Patent References:
| WO2017097220A1 | 2017-06-15 | |||
| WO2011057126A1 | 2011-05-12 | |||
| WO2019143860A1 | 2019-07-25 | |||
| WO2002012235A1 | 2002-02-14 | |||
| WO2007101841A2 | 2007-09-13 |
Foreign References:
| US6528538B1 | 2003-03-04 | |||
| CN104854105A | 2015-08-19 | |||
| US20070265228A1 | 2007-11-15 |
Other References:
LI JING; YUE YONGKANG; HUO FANGJUN; YIN CAIXIA: "Rational design of cysteine-specific ratiometric probe based on steric hindrance effect and its biological application", DYES AND PIGMENTS, vol. 164, 1 January 1900 (1900-01-01), GB, pages 335 - 340, XP085606842, ISSN: 0143-7208, DOI: 10.1016/j.dyepig.2019.01.045
MISHRA UTTAM K., PATEL KAUSHALENDRA, RAMASASTRY S. S. V.: "Synthesis of Cyclopropanoids via Substrate-Based Cyclization Pathways", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, vol. 21, no. 1, 4 January 2019 (2019-01-04), US , pages 175 - 179, XP055921770, ISSN: 1523-7060, DOI: 10.1021/acs.orglett.8b03537
KOBAYASHI KAZUHIRO, KURODA MINAMI: "Synthesis of 3-(ω-Hydroxyalkoxy)isobenzofuran-1(3H)-ones by Trifluoroacetic Acid-Mediated Lactonization of tert-Butyl 2-(1,3-Dioxol-2-yl)- or 2-(1,3-Dioxan-2-yl)benzoates.", HELVETICA CHIMICA ACTA, vol. 97, 31 December 2014 (2014-12-31), pages 1055 - 1060, XP055820648
BUNCE RICHARD A., HARRISON TODD, NAMMALWAR BASKAR: "Efficient synthesis of selected phthalazine derivatives,", HETEROCYCLIC COMMUNICATIONS., vol. 18, no. 3, 31 December 2012 (2012-12-31), DE, pages 123 - 126, XP055820650, ISSN: 0793-0283, DOI: 10.1515/hc-2012-0079
SO WON YOUN, HYOUNG SUB SONG, AND JONG HYUB PARK: "Asymmetric Domino Multicatalysis for the Synthesis of 3-Substituted Phthalides: Cinchonine/NHC Cooperative System,", ORGANIC LETTERS, vol. 16, no. 3, 24 January 2014 (2014-01-24), pages 1028 - 1031, XP009528480, ISSN: 1523-7060, DOI: 10.1021/ol5000617
KLATT THOMAS ET AL.: "Generation of functionalized aryl and heteroaryl aluminum reagents by halogen–lithium exchange,", CHEMICAL COMMUNICATIONS,, vol. 49, no. 62, 12 June 2013 (2013-06-12), XP055367838, DOI: 10.1039/c3cc43356k
GARCIA-GARIBAY MIGUEL A., DANG HUNG: "Photochemical generation, intramolecular reactions, and spectroscopic detection of oxonium ylide and carbene intermediates in a crystalline ortho-(1,3-dioxolan-2-yl)-diaryldiazomethane", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 7, no. 6, 3 February 2009 (2009-02-03), pages 1106 - 114, XP055820965, ISSN: 1477-0520, DOI: 10.1039/b814387k
KURODA, Y. KAWASHIMA, A. URAI, T. OGOSHI, H.: "Self-induced porphyrin dimer formation via unusual atropisomerization of tetraphenylporphyrin derivative", TETRAHEDRON LETTERS, vol. 36, no. 46, 13 November 1995 (1995-11-13), Amsterdam , NL, pages 8449 - 8452, XP005270646, ISSN: 0040-4039, DOI: 10.1016/0040-4039(95)01819-4
SANG CHUL SHIM, DONG YUP LEE, HEUNG JIN CHOI, CHIL HOON DOH, KEUN TAI HUH: "Carbonylation of Protected or Non-protected 2-Bromobenzaldehyde Catalyzed by Cobalt Carbonyl", BULLETIN OF THE KOREAN CHEMICAL SOCIETY, vol. 15, no. 9, 31 December 1994 (1994-12-31), KR, pages 772 - 774, XP055820972, ISSN: 0253-2964
OSUKA ATSUHIRO, NAKAJIMA SATOSHI, MARUYAMA KAZUHIRO: "Synthesis of a 1,2-phenylene-bridged triporphyrin", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 57, no. 26, 1 December 1992 (1992-12-01), pages 7355 - 7359, XP055821031, ISSN: 0022-3263, DOI: 10.1021/jo00052a066
SMITH JAMES G, KRUGER GUNTHER: "Precursors to Isobenzofuran. Monoacetals of o -Phthalaldehyde", J. ORG. CHEM, vol. 50, 31 December 1985 (1985-12-31), pages 5759 - 5760, XP055821032
ANDERSON E; CAPON B: "Intramolecular Nucleophilic Assistance in Reactions of Acetals", JOURNAL OF THE CHEMICAL SOCIETY, 1 January 1972 (1972-01-01), GB, pages 515 - 522, XP009104825, ISSN: 0300-9580, DOI: 10.1039/p29720000515
WHITE, A.W. CURTIN, N.J. EASTMAN, B.W. GOLDING, B.T. HOSTOMSKY, Z. KYLE, S. LI, J. MAEGLEY, K.A. SKALITZKY, D.J. : "Potentiation of cytotoxic drug activity in human tumour cell lines, by amine-substituted 2-arylbenzimidazole-4-carboxamide PARP-1 inhibitors", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 14, no. 10, 17 May 2004 (2004-05-17), AMSTERDAM, NL, pages 2433 - 2437, XP004841215, ISSN: 0960-894X, DOI: 10.1016/j.bmcl.2004.03.017
NICHOLAS ALLEN W.: "Plant Antitumor Agents， 29. Synthesis and Biological Activity of Ring D and Ring E Modified Analogues of Camptothecin", JOURNAL OF MEDICINAL CHEMISTRY, vol. 33, no. 3, 31 December 1990 (1990-12-31), pages 972 - 978, XP055821037
OZORES HAXEL LIONEL, AMORÍN MANUEL, GRANJA JUAN R.: "Self-Assembling Molecular Capsules Based on α,γ-Cyclic Peptides", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, US, vol. 139, no. 2, 18 January 2017 (2017-01-18), US, pages 776 - 784, XP055821039, ISSN: 0002-7863, DOI: 10.1021/jacs.6b10456
SHIM CHUL SANG: "Carbonylation of Bromobenzenes having Aldehyde or Protected Aldehyde Groups Catalyzed by Cobalt Carbonyl(I)", BULLETIN OF THE KOREAN CHEMICAL SOCIETY, vol. 13, no. 4, 31 December 1992 (1992-12-31), pages 444 - 447, XP055821041
N.ACKERLEY ET AL.: "A novel approach to dual-acting thromboxane receptor antagonist/synthase inhibitors based on the link of 1,3-dioxane-Thromboxane receptor antagonists and- thromboxane synthase inhibitors.", JOURNAL OF MEDICINAL CHEMISTRY, vol. 38, 1 January 1995 (1995-01-01), pages 1608 - 1628, XP002450969, ISSN: 0022-2623, DOI: 10.1021/jm00010a005
PLIEGER PAUL G., BURRELL ANTHONY K., JAMESON GEOFFREY B., OFFICER DAVID L.: "Metallation effects on the thermal interconversion of atropisomers of di(orthomethylarene)-substituted porphyrins", DALTON TRANSACTIONS, RSC - ROYAL SOCIETY OF CHEMISTRY, CAMBRIDGE, no. 2, 1 January 2004 (2004-01-01), Cambridge, pages 319 - 326, XP055821043, ISSN: 1477-9226, DOI: 10.1039/b312898a
LAI, G. ; MERRITT, J.R. ; HE, Z. ; FENG, D. ; CHAO, J. ; CZARNIECKI, M.F. ; ROKOSZ, L.L. ; STAUFFER, T.M. ; RINDGEN, D. ; TAVERAS,: "Synthesis and structure-activity relationships of new disubstituted phenyl-containing 3,4-diamino-3-cyclobutene-1,2-diones as CXCR2 receptor antagonists", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 18, no. 6, 15 March 2008 (2008-03-15), AMSTERDAM, NL, pages 1864 - 1868, XP025694983, ISSN: 0960-894X, DOI: 10.1016/j.bmcl.2008.02.010
DATABASE REGISTRY 19 December 2007 (2007-12-19), ANONYMOUS: "/1 -(C) FILE REGISTRY RN -958799-95-6 REGISTRY ED -Entered STN: 19 Dec 2007 CN -Benzoic acid, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)-, methyl ester (CA INDEX NAME)", XP055821047, retrieved from STN Database accession no. 958799-95-6
DATABASE REGISTRY 10 March 2011 (2011-03-10), ANONYMOUS: "/1 -(C) FILE REGISTRY RN -1268137-44-5 REGISTRY ED -Entered STN: 10 Mar 2011 CN -1-Butanone, 1-[3-(1,3-dioxolan-2-yl)phenyl]-3-methyl- (CA INDEX NAME)", XP055821053, retrieved from STN Database accession no. 1268137-44-5
DATABASE REGISTRY 9 March 2011 (2011-03-09), ANONYMOUS: "/1 -(C) FILE REGISTRY RN -1267533-91-4 REGISTRY ED -Entered STN: 09 Mar 2011 CN -1-Propanone, 1-[3-(1,3-dioxolan-2-yl)phenyl]-2,2-dimethyl- (CA INDEX NAME)", XP055821087, retrieved from STN Database accession no. 1267533-91-4
See also references of EP 4073021A4
MISHRA UTTAM K., PATEL KAUSHALENDRA, RAMASASTRY S. S. V.: "Synthesis of Cyclopropanoids via Substrate-Based Cyclization Pathways", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, vol. 21, no. 1, 4 January 2019 (2019-01-04), US , pages 175 - 179, XP055921770, ISSN: 1523-7060, DOI: 10.1021/acs.orglett.8b03537
KOBAYASHI KAZUHIRO, KURODA MINAMI: "Synthesis of 3-(ω-Hydroxyalkoxy)isobenzofuran-1(3H)-ones by Trifluoroacetic Acid-Mediated Lactonization of tert-Butyl 2-(1,3-Dioxol-2-yl)- or 2-(1,3-Dioxan-2-yl)benzoates.", HELVETICA CHIMICA ACTA, vol. 97, 31 December 2014 (2014-12-31), pages 1055 - 1060, XP055820648
BUNCE RICHARD A., HARRISON TODD, NAMMALWAR BASKAR: "Efficient synthesis of selected phthalazine derivatives,", HETEROCYCLIC COMMUNICATIONS., vol. 18, no. 3, 31 December 2012 (2012-12-31), DE, pages 123 - 126, XP055820650, ISSN: 0793-0283, DOI: 10.1515/hc-2012-0079
SO WON YOUN, HYOUNG SUB SONG, AND JONG HYUB PARK: "Asymmetric Domino Multicatalysis for the Synthesis of 3-Substituted Phthalides: Cinchonine/NHC Cooperative System,", ORGANIC LETTERS, vol. 16, no. 3, 24 January 2014 (2014-01-24), pages 1028 - 1031, XP009528480, ISSN: 1523-7060, DOI: 10.1021/ol5000617
KLATT THOMAS ET AL.: "Generation of functionalized aryl and heteroaryl aluminum reagents by halogen–lithium exchange,", CHEMICAL COMMUNICATIONS,, vol. 49, no. 62, 12 June 2013 (2013-06-12), XP055367838, DOI: 10.1039/c3cc43356k
GARCIA-GARIBAY MIGUEL A., DANG HUNG: "Photochemical generation, intramolecular reactions, and spectroscopic detection of oxonium ylide and carbene intermediates in a crystalline ortho-(1,3-dioxolan-2-yl)-diaryldiazomethane", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 7, no. 6, 3 February 2009 (2009-02-03), pages 1106 - 114, XP055820965, ISSN: 1477-0520, DOI: 10.1039/b814387k
KURODA, Y. KAWASHIMA, A. URAI, T. OGOSHI, H.: "Self-induced porphyrin dimer formation via unusual atropisomerization of tetraphenylporphyrin derivative", TETRAHEDRON LETTERS, vol. 36, no. 46, 13 November 1995 (1995-11-13), Amsterdam , NL, pages 8449 - 8452, XP005270646, ISSN: 0040-4039, DOI: 10.1016/0040-4039(95)01819-4
SANG CHUL SHIM, DONG YUP LEE, HEUNG JIN CHOI, CHIL HOON DOH, KEUN TAI HUH: "Carbonylation of Protected or Non-protected 2-Bromobenzaldehyde Catalyzed by Cobalt Carbonyl", BULLETIN OF THE KOREAN CHEMICAL SOCIETY, vol. 15, no. 9, 31 December 1994 (1994-12-31), KR, pages 772 - 774, XP055820972, ISSN: 0253-2964
OSUKA ATSUHIRO, NAKAJIMA SATOSHI, MARUYAMA KAZUHIRO: "Synthesis of a 1,2-phenylene-bridged triporphyrin", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 57, no. 26, 1 December 1992 (1992-12-01), pages 7355 - 7359, XP055821031, ISSN: 0022-3263, DOI: 10.1021/jo00052a066
SMITH JAMES G, KRUGER GUNTHER: "Precursors to Isobenzofuran. Monoacetals of o -Phthalaldehyde", J. ORG. CHEM, vol. 50, 31 December 1985 (1985-12-31), pages 5759 - 5760, XP055821032
ANDERSON E; CAPON B: "Intramolecular Nucleophilic Assistance in Reactions of Acetals", JOURNAL OF THE CHEMICAL SOCIETY, 1 January 1972 (1972-01-01), GB, pages 515 - 522, XP009104825, ISSN: 0300-9580, DOI: 10.1039/p29720000515
WHITE, A.W. CURTIN, N.J. EASTMAN, B.W. GOLDING, B.T. HOSTOMSKY, Z. KYLE, S. LI, J. MAEGLEY, K.A. SKALITZKY, D.J. : "Potentiation of cytotoxic drug activity in human tumour cell lines, by amine-substituted 2-arylbenzimidazole-4-carboxamide PARP-1 inhibitors", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 14, no. 10, 17 May 2004 (2004-05-17), AMSTERDAM, NL, pages 2433 - 2437, XP004841215, ISSN: 0960-894X, DOI: 10.1016/j.bmcl.2004.03.017
NICHOLAS ALLEN W.: "Plant Antitumor Agents， 29. Synthesis and Biological Activity of Ring D and Ring E Modified Analogues of Camptothecin", JOURNAL OF MEDICINAL CHEMISTRY, vol. 33, no. 3, 31 December 1990 (1990-12-31), pages 972 - 978, XP055821037
OZORES HAXEL LIONEL, AMORÍN MANUEL, GRANJA JUAN R.: "Self-Assembling Molecular Capsules Based on α,γ-Cyclic Peptides", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, US, vol. 139, no. 2, 18 January 2017 (2017-01-18), US, pages 776 - 784, XP055821039, ISSN: 0002-7863, DOI: 10.1021/jacs.6b10456
SHIM CHUL SANG: "Carbonylation of Bromobenzenes having Aldehyde or Protected Aldehyde Groups Catalyzed by Cobalt Carbonyl(I)", BULLETIN OF THE KOREAN CHEMICAL SOCIETY, vol. 13, no. 4, 31 December 1992 (1992-12-31), pages 444 - 447, XP055821041
N.ACKERLEY ET AL.: "A novel approach to dual-acting thromboxane receptor antagonist/synthase inhibitors based on the link of 1,3-dioxane-Thromboxane receptor antagonists and- thromboxane synthase inhibitors.", JOURNAL OF MEDICINAL CHEMISTRY, vol. 38, 1 January 1995 (1995-01-01), pages 1608 - 1628, XP002450969, ISSN: 0022-2623, DOI: 10.1021/jm00010a005
PLIEGER PAUL G., BURRELL ANTHONY K., JAMESON GEOFFREY B., OFFICER DAVID L.: "Metallation effects on the thermal interconversion of atropisomers of di(orthomethylarene)-substituted porphyrins", DALTON TRANSACTIONS, RSC - ROYAL SOCIETY OF CHEMISTRY, CAMBRIDGE, no. 2, 1 January 2004 (2004-01-01), Cambridge, pages 319 - 326, XP055821043, ISSN: 1477-9226, DOI: 10.1039/b312898a
LAI, G. ; MERRITT, J.R. ; HE, Z. ; FENG, D. ; CHAO, J. ; CZARNIECKI, M.F. ; ROKOSZ, L.L. ; STAUFFER, T.M. ; RINDGEN, D. ; TAVERAS,: "Synthesis and structure-activity relationships of new disubstituted phenyl-containing 3,4-diamino-3-cyclobutene-1,2-diones as CXCR2 receptor antagonists", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 18, no. 6, 15 March 2008 (2008-03-15), AMSTERDAM, NL, pages 1864 - 1868, XP025694983, ISSN: 0960-894X, DOI: 10.1016/j.bmcl.2008.02.010
DATABASE REGISTRY 19 December 2007 (2007-12-19), ANONYMOUS: "/1 -(C) FILE REGISTRY RN -958799-95-6 REGISTRY ED -Entered STN: 19 Dec 2007 CN -Benzoic acid, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)-, methyl ester (CA INDEX NAME)", XP055821047, retrieved from STN Database accession no. 958799-95-6
DATABASE REGISTRY 10 March 2011 (2011-03-10), ANONYMOUS: "/1 -(C) FILE REGISTRY RN -1268137-44-5 REGISTRY ED -Entered STN: 10 Mar 2011 CN -1-Butanone, 1-[3-(1,3-dioxolan-2-yl)phenyl]-3-methyl- (CA INDEX NAME)", XP055821053, retrieved from STN Database accession no. 1268137-44-5
DATABASE REGISTRY 9 March 2011 (2011-03-09), ANONYMOUS: "/1 -(C) FILE REGISTRY RN -1267533-91-4 REGISTRY ED -Entered STN: 09 Mar 2011 CN -1-Propanone, 1-[3-(1,3-dioxolan-2-yl)phenyl]-2,2-dimethyl- (CA INDEX NAME)", XP055821087, retrieved from STN Database accession no. 1267533-91-4
See also references of EP 4073021A4
Attorney, Agent or Firm:
CHINA PATENT AGENT (H.K.) LTD. (CN)
Download PDF: