MD4515C1 - Process for producing (Z)-4,4-dimethyl-1-(4-nitrophenyl)-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-one - Google Patents
Process for producing (Z)-4,4-dimethyl-1-(4-nitrophenyl)-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-one Download PDFInfo
- Publication number
- MD4515C1 MD4515C1 MDA20160145A MD20160145A MD4515C1 MD 4515 C1 MD4515 C1 MD 4515C1 MD A20160145 A MDA20160145 A MD A20160145A MD 20160145 A MD20160145 A MD 20160145A MD 4515 C1 MD4515 C1 MD 4515C1
- Authority
- MD
- Moldova
- Prior art keywords
- triazol
- dimethyl
- pent
- nitrophenyl
- producing
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- HSYXNSUUVTWJTP-JYRVWZFOSA-N (z)-4,4-dimethyl-1-(4-nitrophenyl)-2-(1,2,4-triazol-1-yl)pent-1-en-3-one Chemical compound C1=NC=NN1/C(C(=O)C(C)(C)C)=C\C1=CC=C([N+]([O-])=O)C=C1 HSYXNSUUVTWJTP-JYRVWZFOSA-N 0.000 title abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- VRDBIJCCXDEZJN-UHFFFAOYSA-N 2-piperidin-1-ylacetic acid Chemical compound OC(=O)CN1CCCCC1 VRDBIJCCXDEZJN-UHFFFAOYSA-N 0.000 abstract 1
- FMWWRALTYIWZEB-UHFFFAOYSA-N 3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound CC(C)(C)C(=O)CN1C=NC=N1 FMWWRALTYIWZEB-UHFFFAOYSA-N 0.000 abstract 1
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 abstract 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 abstract 1
- 230000002365 anti-tubercular Effects 0.000 abstract 1
- 238000010533 azeotropic distillation Methods 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 230000000707 stereoselective effect Effects 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 201000008827 tuberculosis Diseases 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention relates to pharmaceutical chemistry and can be used in the development of new agents for the treatment of tuberculosis from the 1,2,4-triazole class.Summary of the invention consists in that a simple stereoselective method for the synthesis of (Z)-4,4-dimethyl-1-(4-nitrophenyl)-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-one is proposed, which exhibits antituberculous activity, with the formula:.The method provides the aldol-crotonic condensation of 3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one with 4-nitrobenzaldehyde, which runs during reflux in benzene, with azeotropic distillation of the formed water, in the presence of a piperidine-acetic acid catalyst. The starting reagents and the reaction conditions lead to the production of only one single geometric isomer Z (70%, m.p. 114…116°C).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20160145A MD4515C1 (en) | 2016-12-21 | 2016-12-21 | Process for producing (Z)-4,4-dimethyl-1-(4-nitrophenyl)-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-one |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20160145A MD4515C1 (en) | 2016-12-21 | 2016-12-21 | Process for producing (Z)-4,4-dimethyl-1-(4-nitrophenyl)-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-one |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MD4515B1 MD4515B1 (en) | 2017-09-30 |
| MD4515C1 true MD4515C1 (en) | 2018-04-30 |
Family
ID=59974073
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MDA20160145A MD4515C1 (en) | 2016-12-21 | 2016-12-21 | Process for producing (Z)-4,4-dimethyl-1-(4-nitrophenyl)-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-one |
Country Status (1)
| Country | Link |
|---|---|
| MD (1) | MD4515C1 (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1168248A (en) * | 1980-07-25 | 1984-05-29 | Erik Regel | Triazolylpropenol derivatives, a process for their preparation and their use as plant growth regulators and fungicides |
| CA1179352A (en) * | 1980-07-25 | 1984-12-11 | Erik Regel | Triazolylpropenone derivatives, a process for their preparation and their use as intermediates |
| US4554007A (en) * | 1979-03-20 | 1985-11-19 | Sumitomo Chemical Company, Limited | Geometrical isomer of 1-substituted-1-triazolylstyrenes, and their production and use as fungicide, herbicide and/or plant growth regulant |
-
2016
- 2016-12-21 MD MDA20160145A patent/MD4515C1/en not_active IP Right Cessation
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4554007A (en) * | 1979-03-20 | 1985-11-19 | Sumitomo Chemical Company, Limited | Geometrical isomer of 1-substituted-1-triazolylstyrenes, and their production and use as fungicide, herbicide and/or plant growth regulant |
| US4749716A (en) * | 1979-03-20 | 1988-06-07 | Sumitomo Chemical Company, Limited | Geometrical isomer of 1-substituted-1-triazolystyrenes |
| CA1168248A (en) * | 1980-07-25 | 1984-05-29 | Erik Regel | Triazolylpropenol derivatives, a process for their preparation and their use as plant growth regulators and fungicides |
| CA1179352A (en) * | 1980-07-25 | 1984-12-11 | Erik Regel | Triazolylpropenone derivatives, a process for their preparation and their use as intermediates |
Non-Patent Citations (3)
| Title |
|---|
| Funaki Y., Ishiguri Y., Kato T. and Tanaka S. Structure-Activity Relationships of Vinyl Triazole Fungicide. J. Pesticide Sci. 9, 229-236 (1984), regăsit în Internet la 2017.06.08, url: https://www.jstage.jst.go.jp/article/jpestics1975/9/2/9_2_229/_pdf, p. 229, 230; table 1, compounds 7 and 15 * |
| Pawan Kumar Mishra, Jaya Dwivedi, Rajani Chauhan. Triazoles as potential antitubercular agent: a review. Journal of Advanced Scientific Research, 2016, v. 7(1), p. 9-13 * |
| Rangappa S. Keri, Siddappa A. Patil, Srinivasa Budagumpi, Bhari Mallanna Nagaraja. Triazole: A Promising Antitubercular Agent. Chem Biol Drug Des, 2015, v. 86, p. 410-423 * |
Also Published As
| Publication number | Publication date |
|---|---|
| MD4515B1 (en) | 2017-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG4A | Patent for invention issued | ||
| KA4A | Patent for invention lapsed due to non-payment of fees (with right of restoration) | ||
| MM4A | Patent for invention definitely lapsed due to non-payment of fees |