Title:
PROCESS FOR THE PREPARATION OF CINNAMALDEHYDE COMPOUNDS
Document Type and Number:
WIPO Patent Application WO2005000777
Kind Code:
A3
Abstract:
A process for the preparation of cinnamaldehyde, a,ß-unsaturated cyanoester, and cyanoamide compounds using a Heck reaction is described. Methods for further elaboration of these aldehydes are also provided.
Inventors:
RUHA OLIVIER (CH)
OSWALD THOMAS (CH)
OSWALD THOMAS (CH)
Application Number:
PCT/IB2004/002153
Publication Date:
April 14, 2005
Filing Date:
June 29, 2004
Export Citation:
Assignee:
LYMPHOSIGN INC (CA)
RUHA OLIVIER (CH)
OSWALD THOMAS (CH)
RUHA OLIVIER (CH)
OSWALD THOMAS (CH)
International Classes:
C07C45/59; C07C45/67; C07C47/27; C07D317/50; C07F9/40; (IPC1-7): C07C45/45; C07C47/27; C07C253/30; C07C255/41; C07C255/42
Domestic Patent References:
| WO2001079158A2 | 2001-10-25 |
Foreign References:
| US3783140A | 1974-01-01 |
Other References:
GUPTA, ARUN KUMAR ET AL: "1-(2-Iodophenyl)-1H-tetrazole as a ligand for Pd (II)-catalyzed Heck reaction", TETRAHEDRON LETTERS , 45(21), 4113-4116 CODEN: TELEAY; ISSN: 0040-4039, 2004, XP002295282
BATTISTUZZI, GIANFRANCO ET AL: "An Efficient Palladium -Catalyzed Synthesis of Cinnamaldehydes from Acrolein Diethyl Acetal and Aryl Iodides and Bromides", ORGANIC LETTERS , 5(5), 777-780 CODEN: ORLEF7; ISSN: 1523-7060, 2003, XP002295283
ZHAO, LIGANG ET AL: "Palladium (II)-Catalyzed Three-Component Coupling Reaction Initiated by Acetoxypalladation of Alkynes: An Efficient Route to .gamma.,.delta.-Unsaturated Carbonyls", ORGANIC LETTERS , 4(22), 3903-3906 CODEN: ORLEF7; ISSN: 1523-7060, 2002, XP002295284
DATABASE CHEMABS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; HIRABAYASHI, KAZUNORI ET AL: "Novel Carbon-Carbon Bond Formation through Mizoroki-Heck Type Reaction of Silanols and Organotin Compounds", XP002295286, retrieved from STN Database accession no. 2000:388440
NISHIBAYASHI, YOSHIAKI ET AL: "Palladium -catalyzed cross-coupling reactions between organic tellurides and alkenes", JOURNAL OF ORGANOMETALLIC CHEMISTRY , 507(1-2), 197-200 CODEN: JORCAI; ISSN: 0022-328X, 1996, XP002295285
DATABASE CHEMABS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; LEE, JONG TAE ET AL: "Synthesis of conjugated dienals by palladium -catalyzed vinyl substitution reaction", XP002295287, retrieved from STN Database accession no. 1985:5825
BUMA W J ET AL: "THE LOWEST EXCITED SINGLET STATE OF ISOLATED 1-PHENYL-1,3-BUTADIENE AND 1-PHENYL-1,3,5-HEXATRIENE", JOURNAL OF CHEMICAL PHYSICS, NEW YORK, NY, US, vol. 96, no. 7, 1 April 1992 (1992-04-01), pages 4860 - 4868, XP008025606, ISSN: 0021-9606
DATABASE BEILSTEIN [online] BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; 1976, XP002295288, retrieved from XFIRE accession no. BRN2086635
DATABASE BEILSTEIN [online] BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; 1928, XP002295289, retrieved from XFIRE accession no. BRN3127190
BATTISTUZZI, GIANFRANCO ET AL: "An Efficient Palladium -Catalyzed Synthesis of Cinnamaldehydes from Acrolein Diethyl Acetal and Aryl Iodides and Bromides", ORGANIC LETTERS , 5(5), 777-780 CODEN: ORLEF7; ISSN: 1523-7060, 2003, XP002295283
ZHAO, LIGANG ET AL: "Palladium (II)-Catalyzed Three-Component Coupling Reaction Initiated by Acetoxypalladation of Alkynes: An Efficient Route to .gamma.,.delta.-Unsaturated Carbonyls", ORGANIC LETTERS , 4(22), 3903-3906 CODEN: ORLEF7; ISSN: 1523-7060, 2002, XP002295284
DATABASE CHEMABS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; HIRABAYASHI, KAZUNORI ET AL: "Novel Carbon-Carbon Bond Formation through Mizoroki-Heck Type Reaction of Silanols and Organotin Compounds", XP002295286, retrieved from STN Database accession no. 2000:388440
NISHIBAYASHI, YOSHIAKI ET AL: "Palladium -catalyzed cross-coupling reactions between organic tellurides and alkenes", JOURNAL OF ORGANOMETALLIC CHEMISTRY , 507(1-2), 197-200 CODEN: JORCAI; ISSN: 0022-328X, 1996, XP002295285
DATABASE CHEMABS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; LEE, JONG TAE ET AL: "Synthesis of conjugated dienals by palladium -catalyzed vinyl substitution reaction", XP002295287, retrieved from STN Database accession no. 1985:5825
BUMA W J ET AL: "THE LOWEST EXCITED SINGLET STATE OF ISOLATED 1-PHENYL-1,3-BUTADIENE AND 1-PHENYL-1,3,5-HEXATRIENE", JOURNAL OF CHEMICAL PHYSICS, NEW YORK, NY, US, vol. 96, no. 7, 1 April 1992 (1992-04-01), pages 4860 - 4868, XP008025606, ISSN: 0021-9606
DATABASE BEILSTEIN [online] BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; 1976, XP002295288, retrieved from XFIRE accession no. BRN2086635
DATABASE BEILSTEIN [online] BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; 1928, XP002295289, retrieved from XFIRE accession no. BRN3127190
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