Title:
PROCESSES FOR THE 3,3-DIALKYLATION OF 4-CHROMANONES
Document Type and Number:
WIPO Patent Application WO2006089008
Kind Code:
A3
Abstract:
The present invention relates to methods for the preparation of 3,3-dialky 4- chromanones, and particularly to the preparation of 6-fluoro-3,3-dimethyl-2,3-dihydro- 4H-chromen-4-one and 3,3-dimethyl-2,3-dihydro-4H-chromen-4-one. In some embodiments, the processes include reaction of a 4-chromanone compound with an alkyl halide in the presence of a metal alkoxide at low temperature.
Inventors:
YAMASHITA AYAKO (US)
NORTON EMILY B (US)
SHIM JAECHUL (US)
HANNA CILIEN (US)
NORTON EMILY B (US)
SHIM JAECHUL (US)
HANNA CILIEN (US)
Application Number:
PCT/US2006/005449
Publication Date:
December 14, 2006
Filing Date:
February 15, 2006
Export Citation:
Assignee:
WYETH CORP (US)
YAMASHITA AYAKO (US)
NORTON EMILY B (US)
SHIM JAECHUL (US)
HANNA CILIEN (US)
YAMASHITA AYAKO (US)
NORTON EMILY B (US)
SHIM JAECHUL (US)
HANNA CILIEN (US)
International Classes:
C07D309/30
Other References:
LACHAPELLE, A. ET AL: "Conformational analysis of 3-substituted-2,3,4,5-tetrahydro-1- benzoxepin by proton and carbon-13 nuclear magnetic resonance", CANADIAN JOURNAL OF CHEMISTRY , 65(11), 2575-94 CODEN: CJCHAG; ISSN: 0008-4042, 1987, XP009067610
H. E. ZIMMERMAN, R. E. FACTOR: "The Bicycle Rearrangement. Relationship to the Di-pi-methane Rearrangement and Control by Bifunnel Distortion. Mechanistic and Exploratory Organic Photochemistry.", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 102, no. 10, 1980, pages 3538 - 3548, XP002384958
"Alumina-Catalysed Reactions of Hydroxyarenes and Hydroaromatic Ketones. I. Reactions of 1-Naphtol with Methanol.", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 33, no. 4, 1968, XP002384959
AKUAMOAH, ROBERT K. ET AL: "Studies of chromenes. Part 11. 3-Substitution of 7-methoxy-2,2-dimethyl-4-chromanone without ring opening via 3-bromination", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1: ORGANIC AND BIO-ORGANIC CHEMISTRY , (3), 197-201 CODEN: JCPRB4; ISSN: 0300-922X, 1995, XP009067611
CASCAVAL, ALEXANDRU: "2-Hydroxyketones; XII. A simple synthesis of 3,3,6,8- tetrasubstituted 4-chromanones", SYNTHESIS , (7), 579-80 CODEN: SYNTBF; ISSN: 0039-7881, 1983, XP001026049
POONAM PRASAD A K ET AL: "Synthesis and lipase-mediated stereoselective deacetylation of (+/-)-3-acetoxymethyl-3-alkyl-7-methoxychroman-4-ones", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 57, no. 34, 20 August 2001 (2001-08-20), pages 7395 - 7402, XP004301025, ISSN: 0040-4020
CID J M ET AL: "Selective alpha-monoallylation of phenyl ketones and benzocycloalkanones under microwave irradiation", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 45, no. 6, 2 February 2004 (2004-02-02), pages 1133 - 1136, XP004484797, ISSN: 0040-4039
TRIKHA, SMRITI ET AL: "Candida rugosa lipase-mediated enantioselective acetylation studies on (.+-.)-3-arylmethyl-3-hydroxymethyl-2,3-dihydro-1-benzopyran-4(H)- ones", INDIAN JOURNAL OF CHEMISTRY, SECTION B: ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY , 44B(2), 356-365 CODEN: IJSBDB; ISSN: 0376-4699, 2005, XP009071740
FINARU, A. ET AL: "Synthesis of 4-chromanone-type Mannich-Werner bases", JOURNAL DE LA SOCIETE ALGERIENNE DE CHIMIE , 9(1), 85-90 CODEN: JSACEX; ISSN: 1111-4797, 1999, XP009071738
BARLOCCO, DANIELA ET AL: "Hydroxymethylation of 2-hydroxypropiophenones in aqueous medium. Synthesis of 3-(hydroxymethyl)-3-methyl-4-chromanones and their conversion to 3-methyl-4-chromanone-3-acetic acids", SYNTHESIS , (9), 876-8 CODEN: SYNTBF; ISSN: 0039-7881, 1985, XP002398320
AHLUWALIA, V. K. ET AL: "Synthesis of 2-hydroxy-2,3-dihydrochromones and structures of Claisen condensation products of phloracetophenone dimethyl ether and .beta.-orcacetophenone monomethyl ether with ethyl formate", INDIAN JOURNAL OF CHEMISTRY, SECTION B: ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY , 15B(4), 331-4 CODEN: IJSBDB; ISSN: 0376-4699, 1977, XP009071765
ANASTASIS, PANAYIOTIS ET AL: "Studies of chromenes. Part 7. Product stabilization in condensations with 7-methoxy-2,2-dimethylchroman-4-one", JOURNAL OF CHEMICAL RESEARCH, SYNOPSES , (2), 36-7 CODEN: JRPSDC; ISSN: 0308-2342, 1989, XP009067541
YAMASHITA, AYAKO ET AL: "Synthesis of 3,3-Dimethyl-4-chromanones: Improved Procedures Without Ring Opening", SYNTHETIC COMMUNICATIONS , 36(4), 465-472 CODEN: SYNCAV; ISSN: 0039-7911, 2005, XP009067721
H. E. ZIMMERMAN, R. E. FACTOR: "The Bicycle Rearrangement. Relationship to the Di-pi-methane Rearrangement and Control by Bifunnel Distortion. Mechanistic and Exploratory Organic Photochemistry.", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 102, no. 10, 1980, pages 3538 - 3548, XP002384958
"Alumina-Catalysed Reactions of Hydroxyarenes and Hydroaromatic Ketones. I. Reactions of 1-Naphtol with Methanol.", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 33, no. 4, 1968, XP002384959
AKUAMOAH, ROBERT K. ET AL: "Studies of chromenes. Part 11. 3-Substitution of 7-methoxy-2,2-dimethyl-4-chromanone without ring opening via 3-bromination", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1: ORGANIC AND BIO-ORGANIC CHEMISTRY , (3), 197-201 CODEN: JCPRB4; ISSN: 0300-922X, 1995, XP009067611
CASCAVAL, ALEXANDRU: "2-Hydroxyketones; XII. A simple synthesis of 3,3,6,8- tetrasubstituted 4-chromanones", SYNTHESIS , (7), 579-80 CODEN: SYNTBF; ISSN: 0039-7881, 1983, XP001026049
POONAM PRASAD A K ET AL: "Synthesis and lipase-mediated stereoselective deacetylation of (+/-)-3-acetoxymethyl-3-alkyl-7-methoxychroman-4-ones", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 57, no. 34, 20 August 2001 (2001-08-20), pages 7395 - 7402, XP004301025, ISSN: 0040-4020
CID J M ET AL: "Selective alpha-monoallylation of phenyl ketones and benzocycloalkanones under microwave irradiation", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 45, no. 6, 2 February 2004 (2004-02-02), pages 1133 - 1136, XP004484797, ISSN: 0040-4039
TRIKHA, SMRITI ET AL: "Candida rugosa lipase-mediated enantioselective acetylation studies on (.+-.)-3-arylmethyl-3-hydroxymethyl-2,3-dihydro-1-benzopyran-4(H)- ones", INDIAN JOURNAL OF CHEMISTRY, SECTION B: ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY , 44B(2), 356-365 CODEN: IJSBDB; ISSN: 0376-4699, 2005, XP009071740
FINARU, A. ET AL: "Synthesis of 4-chromanone-type Mannich-Werner bases", JOURNAL DE LA SOCIETE ALGERIENNE DE CHIMIE , 9(1), 85-90 CODEN: JSACEX; ISSN: 1111-4797, 1999, XP009071738
BARLOCCO, DANIELA ET AL: "Hydroxymethylation of 2-hydroxypropiophenones in aqueous medium. Synthesis of 3-(hydroxymethyl)-3-methyl-4-chromanones and their conversion to 3-methyl-4-chromanone-3-acetic acids", SYNTHESIS , (9), 876-8 CODEN: SYNTBF; ISSN: 0039-7881, 1985, XP002398320
AHLUWALIA, V. K. ET AL: "Synthesis of 2-hydroxy-2,3-dihydrochromones and structures of Claisen condensation products of phloracetophenone dimethyl ether and .beta.-orcacetophenone monomethyl ether with ethyl formate", INDIAN JOURNAL OF CHEMISTRY, SECTION B: ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY , 15B(4), 331-4 CODEN: IJSBDB; ISSN: 0376-4699, 1977, XP009071765
ANASTASIS, PANAYIOTIS ET AL: "Studies of chromenes. Part 7. Product stabilization in condensations with 7-methoxy-2,2-dimethylchroman-4-one", JOURNAL OF CHEMICAL RESEARCH, SYNOPSES , (2), 36-7 CODEN: JRPSDC; ISSN: 0308-2342, 1989, XP009067541
YAMASHITA, AYAKO ET AL: "Synthesis of 3,3-Dimethyl-4-chromanones: Improved Procedures Without Ring Opening", SYNTHETIC COMMUNICATIONS , 36(4), 465-472 CODEN: SYNCAV; ISSN: 0039-7911, 2005, XP009067721
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