WO1996026202A1 - Verfahren zur herstellung von thietanonen - Google Patents
Verfahren zur herstellung von thietanonen Download PDFInfo
- Publication number
- WO1996026202A1 WO1996026202A1 PCT/EP1996/000391 EP9600391W WO9626202A1 WO 1996026202 A1 WO1996026202 A1 WO 1996026202A1 EP 9600391 W EP9600391 W EP 9600391W WO 9626202 A1 WO9626202 A1 WO 9626202A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- general formula
- formula
- compounds
- base
- thietanones
- Prior art date
Links
- 0 *C(*)C(C(*)(*)N*)=O Chemical compound *C(*)C(C(*)(*)N*)=O 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D331/00—Heterocyclic compounds containing rings of less than five members, having one sulfur atom as the only ring hetero atom
- C07D331/04—Four-membered rings
Definitions
- the invention relates to a process for the preparation of thietanones of the general formula I.
- Arylalkyl are, where the radicals R ⁇ - R 4 where possible and permissible are linear or branched, halogen-substituted and / or N-, O-,
- S-heteroatoms can be substituted and two of the radicals R 1 - R 4 can be connected to form a ring.
- thietanones of the general formula I are used as precursors to substances which are used in dipeptide sweeteners (US Pat. No. 4,692,512, EP-A 168 112, IL-A 63 396, EP-A 128,654, U.S. Patent 4,411,925, U.S. Patent 4,399,163, EP-A 69 811, EP-A 34 876, EP-A 325 485, J. Med. Chem. 1990, 33, 1052).
- the corresponding alcohols (a) are obtained by simple reduction of compounds of the general formula I.
- ester or amide building blocks of dipeptides give compounds (a) and (b) an extreme sweetness.
- the amine (b) gives a building block for alita which has a sweetening power that is about 2000 times greater than that of sugar (ACS Symp. Ser. 1991, 450, 57-67).
- R 1 - R 4 have the meaning given for formula I and
- the cyclization of oxosulfenyl compounds of the general formula II can be carried out in inert organic solvents.
- the preferred solvents according to the invention include, for example, ethers, such as THF, diethyl ether, diisopropyl ether or tertiary butyl ether, (Ci-Ce) alcohols, such as, for example, methanol, ethanol, isopropanol, n-propanol, tert-butanol, n-butanol, n-pentanol or n-hexanol and aliphatic or aromatic hydrocarbons, such as n-hexane, cyclohexane or toluene or mixtures of the solvents mentioned, and alkanes; Solvents such as methanol, ethanol, Isopropanol, butanol and tetrahydrofuran, diethyl ether, diisopropyl ether
- a large number of substances can in principle be used as a base for the cyclization reaction in the context of the invention.
- the preferred compounds to be used include potassium carbonate, sodium hydride and alkali alcoholates.
- the use of KOtBu when using ethers as solvent and when using alcohols is very particularly preferred when using the corresponding sodium alcoholates.
- beta-oxosulfenyl compounds of the general formula II required for the cyclization to thietanones can be prepared by processes known from the literature. From Helv. Chim. Acta 1966, 49, 2344 and J. Prakt. Chem. 1979, 321, 1017 it is known that diisopropyl ketone with
- Disulfides can be reacted with chlorine to the corresponding sulfenyl chlorides (Lit.: Houben Weyl "Methods of Organic Chemistry", Vol. Eil, p. 72ff).
- ⁇ -oxosulfenyl compounds of the formula II can be advantageously used in the context of the invention by reacting ketones of the general formula III
- R 1 - R 4 have the meaning given for formula I, With
- reaction for the preparation of the ⁇ -oxosulfenyl compounds of the formula II can thus be carried out in the context of the invention without a solvent and without the addition of a Lewis acid, which considerably increases the yields given in the literature could.
- Another particularly great advantage is the fact that in the preparation of the oxosulfenyl compound. of the formula II obtained by the process of the invention reaction mixture without further complicated workup simply by dissolving in an organic compound suitable as a solvent.
- the process of the invention is used particularly advantageously for the preparation of 2, 2, 4, 4-tetramethylthietanone.
- this compound in which the radicals R 1 -R 4 all represent a methyl group, has an important position as an intermediate for the production of artificial sweeteners.
- Sulfur dichloride as a compound of the general formula IV or to select disulfur dichloride of the general formula V and chlorine as X 2 for cleavage. These sulfur compounds are safe and easy to handle and allow the production of the ⁇ -oxosulfenyl compounds of the formula II to be cyclized according to the invention in high yield.
- the sulfenyl chloride from Example 5 is in a solution of 1.5 equiv. (based on sulfenyl chloride) sodium methylate added dropwise in methanol. The mixture is then heated under reflux for 3-4 hours. In the heat, one-fifth of the volume is given Add water, let cool and filter off. The ketone is obtained in> 80% yield as a colorless, camphor-like solid.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU47162/96A AU4716296A (en) | 1995-02-21 | 1996-01-31 | Process for producing thietanones |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19505995.6 | 1995-02-21 | ||
DE19505995A DE19505995A1 (de) | 1995-02-21 | 1995-02-21 | Verfahren zur Herstellung von Thietanonen |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1996026202A1 true WO1996026202A1 (de) | 1996-08-29 |
Family
ID=7754643
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1996/000391 WO1996026202A1 (de) | 1995-02-21 | 1996-01-31 | Verfahren zur herstellung von thietanonen |
Country Status (7)
Country | Link |
---|---|
AU (1) | AU4716296A (hr) |
DE (1) | DE19505995A1 (hr) |
HR (1) | HRP960082A2 (hr) |
IL (1) | IL117188A0 (hr) |
WO (1) | WO1996026202A1 (hr) |
YU (1) | YU10196A (hr) |
ZA (1) | ZA961344B (hr) |
Cited By (73)
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WO2005097754A1 (de) * | 2004-04-03 | 2005-10-20 | Bayer Cropscience Gmbh | Herbizid wirksame 3-amino-2 thiomethyl -benzoylpyrazole |
WO2006000592A1 (de) | 2004-06-28 | 2006-01-05 | Basf Aktiengesellschaft | Verwendung von ethergruppen enthaltenden polymeren als lösungsvermittler |
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WO2020057391A1 (zh) | 2018-09-20 | 2020-03-26 | 周银平 | 哒嗪胺类化合物的制备及其应用 |
CN115093391A (zh) * | 2022-06-28 | 2022-09-23 | 上海毕得医药科技股份有限公司 | 一种3-硫杂环丁胺盐酸盐的合成方法 |
-
1995
- 1995-02-21 DE DE19505995A patent/DE19505995A1/de not_active Withdrawn
-
1996
- 1996-01-31 WO PCT/EP1996/000391 patent/WO1996026202A1/de active Application Filing
- 1996-01-31 AU AU47162/96A patent/AU4716296A/en not_active Abandoned
- 1996-02-20 IL IL11718896A patent/IL117188A0/xx unknown
- 1996-02-20 YU YU10196A patent/YU10196A/sh unknown
- 1996-02-20 ZA ZA961344A patent/ZA961344B/xx unknown
- 1996-02-20 HR HR19505995.6A patent/HRP960082A2/hr not_active Application Discontinuation
Non-Patent Citations (8)
Title |
---|
A.P. KOZIKOWSKI ET AL.: "Synthesis of Novel Four-Membered Ring Amino Acids as Modulators of the N-Methyl-D-Aspartate (NMDA) Receptor Complex", SYNLETT, no. 11, 1991, pages 783 - 4, XP000571470 * |
J.S. PIZEY ET AL.: "The reaction between ketones and thionyl chloride", PHOSPHORUS AND SULFUR, vol. 8, no. 1, 1980, pages 1 - 8, XP000196062 * |
M. HARRIS ET AL.: "Reaktionen von Diisopropylketon mit Schwefelchloriden", HELVETICA CHIMICA ACTA, vol. 49/II, no. 5-9, 1966, pages 2344 - 7, XP000571475 * |
M. MÜHLSTÄDT ET AL.: "Beta-Oxosulfenylchloride - Eine neue 5,6-Dihydro-4H-1,2,4-thiadiazin-Synthese", JOURNAL FÜR PRAKTISCHE CHEMIE, vol. 321, no. 6, 1979, pages 1017 - 20, XP000196061 * |
R.J. BUSHBY: "Synthesis of 3-Alkylidene-2,2,4,4-tetramethylthietan 1,1-Dioxides, Possible Precursors of 2-Methylenetrimethylene", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS I, 1975, pages 2513 - 6, XP000571466 * |
T. FURUHATA ET AL.: "Nature of thioxyallyl intermediate in the decomposition of allene episulfide and pyrazoline-4-thione", TETRAHEDRON, vol. 42, no. 19, 1986, pages 5301 - 8, XP000196059 * |
U. LUHMANN ET AL.: "Darstellung und Kristallstruktur von 2,2,5,5-Tetramethyl- 2,3,5,6-tetrahydrothieno[3,2-b]thiophen- 3,6-dion, eines Thioindigo-Grundchromo- phorsystems mit trans-s-trans-s-trans- Konfiguration der Carbonylgruppen", CHEMISCHE BERICHTE, vol. 110, 1977, pages 1421 - 31, XP000196052 * |
W. ANDO ET AL: "Reactions of cyclic disulfides with carbenes; desulfurization and insertion", TETRAHEDRON LETTERS, vol. 26, no. 42, 1985, pages 5187 - 90, XP000196055 * |
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WO2013143927A1 (en) | 2012-03-29 | 2013-10-03 | Basf Se | Co-crystals of dicamba and a co-crystal former b |
WO2013072528A2 (en) | 2012-04-27 | 2013-05-23 | Basf Se | Substituted n-(tetrazol-5-yl)- and n-(triazol-5-yl)pyridin-3-yl-carboxamide compounds and their use as herbicides |
WO2013083859A2 (en) | 2012-04-27 | 2013-06-13 | Basf Se | Substituted n-(tetrazol-5-yl)- and n-(triazol-5-yl)arylcarboxamide compounds and their use as herbicides |
WO2013076316A2 (en) | 2012-04-27 | 2013-05-30 | Basf Se | Substituted n-(tetrazol-5-yl)- and n-(triazol-5-yl)hetarylcarboxamide compounds and their use as herbicides |
WO2013076315A2 (en) | 2012-04-27 | 2013-05-30 | Basf Se | Substituted n-(tetrazol-5-yl)- and n-(triazol-5-yl)arylcarboxamide compounds and their use as herbicides |
US11572571B2 (en) | 2012-06-19 | 2023-02-07 | BASF Agro B.V. | Plants having increased tolerance to herbicides |
US10041087B2 (en) | 2012-06-19 | 2018-08-07 | BASF Agro B.V. | Plants having increased tolerance to herbicides |
US11441154B2 (en) | 2012-06-19 | 2022-09-13 | BASF Agro B.V. | Plants having increased tolerance to herbicides |
US10100329B2 (en) | 2012-06-19 | 2018-10-16 | BASF Agro B.V. | Plants having increased tolerance to herbicides |
WO2014184016A1 (en) | 2013-05-15 | 2014-11-20 | Basf Se | Substituted n-(tetrazol-5-yl)- and n-(triazol-5-yl)arylcarboxamide compounds and their use as herbicides |
WO2014184058A1 (en) | 2013-05-15 | 2014-11-20 | Basf Se | Substituted 1,2,5-oxadiazole compounds and their use as herbicides |
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WO2015007564A1 (en) | 2013-07-18 | 2015-01-22 | Basf Se | Substituted n-(1,2,4-triazol-3-yl)arylcarboxamide compounds and their use as herbicides |
US9926284B2 (en) | 2013-07-18 | 2018-03-27 | Basf Se | Substituted N-(1,2,4-triazol-3-yl)Arylcarboxamide compounds and their use as herbicides |
US11827896B2 (en) | 2013-08-12 | 2023-11-28 | BASF Agro B.V. | Plants having increased tolerance to herbicides |
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US10392630B2 (en) | 2013-08-12 | 2019-08-27 | BASF Agro B.V. | Plants having increased tolerance to herbicides |
US10087460B2 (en) | 2013-08-12 | 2018-10-02 | BASF Agro B.V. | Transgenic or non-transgenic plants with mutated protoporphyrinogen oxidase having increased tolerance to herbicides |
WO2015052178A1 (en) | 2013-10-10 | 2015-04-16 | Basf Se | 1,2,5-oxadiazole compounds and their use as herbicides |
US9902704B2 (en) | 2013-10-10 | 2018-02-27 | Basf Se | Substituted N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamide compounds and their use as herbicides |
WO2015052173A1 (en) | 2013-10-10 | 2015-04-16 | Basf Se | Tetrazole and triazole compounds and their use as herbicides |
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WO2016128470A1 (en) | 2015-02-11 | 2016-08-18 | Basf Se | Herbicide-resistant hydroxyphenylpyruvate dioxygenases |
EP3112016A1 (en) | 2015-07-02 | 2017-01-04 | Basf Se | Microcapsules containing benzoxazinones |
WO2017102275A1 (en) | 2015-12-17 | 2017-06-22 | Basf Se | Benzamide compounds and their use as herbicides |
WO2018219936A1 (en) | 2017-05-30 | 2018-12-06 | Basf Se | Benzamide compounds and their use as herbicides ii |
WO2018219935A1 (en) | 2017-05-30 | 2018-12-06 | Basf Se | Benzamide compounds and their use as herbicides |
WO2018234371A1 (en) | 2017-06-20 | 2018-12-27 | Basf Se | BENZAMIDE COMPOUNDS AND THEIR USE AS HERBICIDES |
WO2019016385A1 (en) | 2017-07-21 | 2019-01-24 | Basf Se | BENZAMIDE COMPOUNDS AND THEIR USE AS HERBICIDES |
WO2019105995A1 (en) | 2017-11-29 | 2019-06-06 | Basf Se | Benzamide compounds and their use as herbicides |
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WO2019122345A1 (en) | 2017-12-22 | 2019-06-27 | Basf Se | Benzamide compounds and their use as herbicides |
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EP3508480A1 (en) | 2018-01-08 | 2019-07-10 | Basf Se | Benzamide compounds and their use as herbicides |
WO2019162309A1 (en) | 2018-02-21 | 2019-08-29 | Basf Se | Benzamide compounds and their use as herbicides |
WO2019162308A1 (en) | 2018-02-21 | 2019-08-29 | Basf Se | Benzamide compounds and their use as herbicides |
WO2020057391A1 (zh) | 2018-09-20 | 2020-03-26 | 周银平 | 哒嗪胺类化合物的制备及其应用 |
CN115093391A (zh) * | 2022-06-28 | 2022-09-23 | 上海毕得医药科技股份有限公司 | 一种3-硫杂环丁胺盐酸盐的合成方法 |
CN115093391B (zh) * | 2022-06-28 | 2024-05-03 | 上海毕得医药科技股份有限公司 | 一种3-硫杂环丁胺盐酸盐的合成方法 |
Also Published As
Publication number | Publication date |
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DE19505995A1 (de) | 1996-08-22 |
YU10196A (sh) | 1998-08-14 |
ZA961344B (en) | 1996-08-26 |
IL117188A0 (en) | 1996-06-18 |
HRP960082A2 (en) | 1997-08-31 |
AU4716296A (en) | 1996-09-11 |
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