DE1670532A1 - [2-(5-Nitro-2-furyl)-vinyl]-pyrimidin-Derivate und Verfahren zu deren Herstellung - Google Patents
[2-(5-Nitro-2-furyl)-vinyl]-pyrimidin-Derivate und Verfahren zu deren HerstellungInfo
- Publication number
- DE1670532A1 DE1670532A1 DE19661670532 DE1670532A DE1670532A1 DE 1670532 A1 DE1670532 A1 DE 1670532A1 DE 19661670532 DE19661670532 DE 19661670532 DE 1670532 A DE1670532 A DE 1670532A DE 1670532 A1 DE1670532 A1 DE 1670532A1
- Authority
- DE
- Germany
- Prior art keywords
- nitro
- furyl
- vinyl
- amino
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 3
- QYWCIRZOGSMFAW-UHFFFAOYSA-N 2-[2-(5-nitrofuran-2-yl)ethenyl]pyrimidine Chemical class O1C([N+](=O)[O-])=CC=C1C=CC1=NC=CC=N1 QYWCIRZOGSMFAW-UHFFFAOYSA-N 0.000 title 1
- -1 5-nitro-2-furyl Chemical group 0.000 claims description 15
- NDSTUUPEXNCUNW-UHFFFAOYSA-N (5-nitrofuran-2-yl)methanol Chemical compound OCC1=CC=C([N+]([O-])=O)O1 NDSTUUPEXNCUNW-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000003230 pyrimidines Chemical class 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims 2
- QWIDYOLZFAQBOB-UHFFFAOYSA-N 2-methyl-1h-pyrimidin-6-one Chemical class CC1=NC=CC(=O)N1 QWIDYOLZFAQBOB-UHFFFAOYSA-N 0.000 claims 2
- 229920002554 vinyl polymer Polymers 0.000 claims 2
- PYNWYHTWXORCCN-UHFFFAOYSA-N 4-methoxy-6-methyl-2-methylsulfanylpyrimidine Chemical compound COC1=CC(C)=NC(SC)=N1 PYNWYHTWXORCCN-UHFFFAOYSA-N 0.000 claims 1
- LVILGAOSPDLNRM-UHFFFAOYSA-N 4-methylpyrimidine Chemical compound CC1=CC=NC=N1 LVILGAOSPDLNRM-UHFFFAOYSA-N 0.000 claims 1
- LHRIUKSRPHFASO-UHFFFAOYSA-N 6-methyl-1h-pyrimidin-4-one Chemical compound CC1=CC(=O)N=CN1 LHRIUKSRPHFASO-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012024 dehydrating agents Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 241000193998 Streptococcus pneumoniae Species 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- MZRSJDMSWGRMJI-UHFFFAOYSA-N (3-nitrofuran-2-yl)methanol Chemical compound OCC=1OC=CC=1[N+]([O-])=O MZRSJDMSWGRMJI-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- OFPWIXYGAJDWPC-UHFFFAOYSA-N 2-ethyl-1h-pyrimidin-6-one Chemical compound CCC1=NC=CC(=O)N1 OFPWIXYGAJDWPC-UHFFFAOYSA-N 0.000 description 1
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- 241000588722 Escherichia Species 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- 241000186781 Listeria Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010037075 Protozoal infections Diseases 0.000 description 1
- 241000531795 Salmonella enterica subsp. enterica serovar Paratyphi A Species 0.000 description 1
- 241000607762 Shigella flexneri Species 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 241000191963 Staphylococcus epidermidis Species 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000000842 anti-protozoal effect Effects 0.000 description 1
- 230000001572 anti-trichomonad Effects 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- AFICWHSZTIGSPG-UHFFFAOYSA-N furan-2-yl(nitro)methanol Chemical compound [O-][N+](=O)C(O)C1=CC=CO1 AFICWHSZTIGSPG-UHFFFAOYSA-N 0.000 description 1
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B51/00—Nitro or nitroso dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5349765 | 1965-09-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1670532A1 true DE1670532A1 (de) | 1970-11-12 |
Family
ID=12944456
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661670532 Pending DE1670532A1 (de) | 1965-09-01 | 1966-08-31 | [2-(5-Nitro-2-furyl)-vinyl]-pyrimidin-Derivate und Verfahren zu deren Herstellung |
Country Status (4)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2839224A1 (de) * | 1977-09-09 | 1979-03-22 | Inst Organicheskogo Sinteza Ak | Substituierte 2- eckige klammer auf 2'-(5''-nitrofuryl-2'')vinyl- und 4-(5''- nitrofuryl-2'')-1,3-butadienyl eckige klammer zu chinolin-4-karbonsaeureamide und deren salze |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL121061C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1962-03-28 |
-
1966
- 1966-08-22 US US573877A patent/US3464982A/en not_active Expired - Lifetime
- 1966-08-23 GB GB37801/66A patent/GB1113382A/en not_active Expired
- 1966-08-31 DE DE19661670532 patent/DE1670532A1/de active Pending
- 1966-09-01 FR FR74900A patent/FR5707M/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2839224A1 (de) * | 1977-09-09 | 1979-03-22 | Inst Organicheskogo Sinteza Ak | Substituierte 2- eckige klammer auf 2'-(5''-nitrofuryl-2'')vinyl- und 4-(5''- nitrofuryl-2'')-1,3-butadienyl eckige klammer zu chinolin-4-karbonsaeureamide und deren salze |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1113382A (en) | 1968-05-15 |
| US3464982A (en) | 1969-09-02 |
| FR5707M (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1968-01-15 |
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