MD4515C1 - Procedeu de obţinere a (Z)-4,4-dimetil-1-(4-nitrofenil)-2-(1H-1,2,4-triazol-1-il)pent-1-en-3-onei - Google Patents
Procedeu de obţinere a (Z)-4,4-dimetil-1-(4-nitrofenil)-2-(1H-1,2,4-triazol-1-il)pent-1-en-3-onei 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
Invenţia se referă la chimia farmaceutică şi poate fi aplicată în extinderea efectivului de remedii noi pentru tratamentul tuberculozei din clasa 1,2,4-triazolului.Esenţa invenţiei constă în aceea că se propune un procedeu stereoselectiv simplu de sinteză, a (Z)-4,4-dimetil-1-(4-nitrofenil)-2-(1H-1,2,4-triazol-1-il)pent-1-en-3-onei, care manifestă o activitate antituberculoasă, cu formula:.Procedeul prevede condensarea aldol-crotonică a 3,3-dimetil-1-(1H-1,2,4-triazol-1-il)butan-2-onei cu aldehida 4-nitrobenzoică, care se efectuează la refluxare în benzen, cu eliminarea azeotropică a apei formate, în prezenţa catalizatorului piperidină-acid acetic. Reagenţii iniţiali şi condiţiile reacţiei duc la formarea doar a unui singur isomer geometric Z (70%, p.t. 114…116°С).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20160145A MD4515C1 (ro) | 2016-12-21 | 2016-12-21 | Procedeu de obţinere a (Z)-4,4-dimetil-1-(4-nitrofenil)-2-(1H-1,2,4-triazol-1-il)pent-1-en-3-onei |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20160145A MD4515C1 (ro) | 2016-12-21 | 2016-12-21 | Procedeu de obţinere a (Z)-4,4-dimetil-1-(4-nitrofenil)-2-(1H-1,2,4-triazol-1-il)pent-1-en-3-onei |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MD4515B1 MD4515B1 (ro) | 2017-09-30 |
| MD4515C1 true MD4515C1 (ro) | 2018-04-30 |
Family
ID=59974073
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MDA20160145A MD4515C1 (ro) | 2016-12-21 | 2016-12-21 | Procedeu de obţinere a (Z)-4,4-dimetil-1-(4-nitrofenil)-2-(1H-1,2,4-triazol-1-il)pent-1-en-3-onei |
Country Status (1)
| Country | Link |
|---|---|
| MD (1) | MD4515C1 (ro) |
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/ro 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 (ro) | 2017-09-30 |
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| 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 |