ES447116A1 - A procedure for preparing 2,4,5,6-tetrahidrociclopenta (c) pirrol-4-carbonitrilos. (Machine-translation by Google Translate, not legally binding) - Google Patents
A procedure for preparing 2,4,5,6-tetrahidrociclopenta (c) pirrol-4-carbonitrilos. (Machine-translation by Google Translate, not legally binding)Info
- Publication number
- ES447116A1 ES447116A1 ES447116A ES447116A ES447116A1 ES 447116 A1 ES447116 A1 ES 447116A1 ES 447116 A ES447116 A ES 447116A ES 447116 A ES447116 A ES 447116A ES 447116 A1 ES447116 A1 ES 447116A1
- Authority
- ES
- Spain
- Prior art keywords
- lower alkyl
- phenyl
- alkyl
- formula
- alkoxy
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 18
- -1 9-acridinyl Chemical group 0.000 abstract 15
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 abstract 1
- VXKHYOYHHMPFGM-UHFFFAOYSA-N 2,4,5,6-tetrahydrocyclopenta[c]pyrrole Chemical group N1C=C2CCCC2=C1 VXKHYOYHHMPFGM-UHFFFAOYSA-N 0.000 abstract 1
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 abstract 1
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 abstract 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 abstract 1
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000005518 carboxamido group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 abstract 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 abstract 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 abstract 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 abstract 1
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for preparing 2,4,5,6-tetrahydrocyclopenta [c] pyrrole-4-carbonitriles having formula II ** (See formula) ** wherein R3, R4 and R5 are each methyl; each group is the same or different and is lower alkyl, hydroxymethyl, or phenyl-lower alkyl; and R7 is hydrogen, lower alkyl, halo-lower alkyl, lower alkenyl, lower alkynyl, di-lower alkylamino-lower alkyl, morpholino-lower alkyl, 1-pyrrolidyl-lower alkyl, 1-piperiayl-lower alkyl, carbo-lower alkoxy -lower alkyl, carboxy-lower alkyl, carboxamido-lower alkyl, triocarboxamido-lower alkyl, lower alkoxy-lower alkyl, hydroxy-lower alkyl, lower alkylthio-lower alkyl, cycloalkyl, cyclo-lower alkyl-alkyl, 2- or 3-pyridyl, phenyl, phenyl-lower alkyl thienyl, cyano-lower alkyl, 9-acridinyl, 4- (2,1,3, -benzotisdiasolyl), 2-benzothiazolyl, 3-carbazolyl, 2-benzoxazolyl, 2- or 6-purinyl, 2-pyrazinyl, 4-pyrimidinyl, 2-thiazolyl, 3-pyrazolyl, 2- or 6-pyrimidinyl, 2-benzimidazolyl, 2-benzothiazoyl, 3-triacinyl, 5-, 6-or 7-indazolyl, 5-isoquinolyl, 3 -pyridazinyl, 2-thiadiozolyl, 5-tetrazolyl, 2-thiazolinyl 3- (1,2,4, -triazinyl, 3- (1,2,4-triazolyl), or lower alkylene divelent e which has its valencies at different carbon atoms and which joins two of the 2,4,5,6-tetrahydrocyclopenta [c] pyrrole moieties to each other, and wherein the phenyl or phenyl-lower alkyl groups can be further substituted in the phenyl nucleus by 1 to 3 members of the group consisting of lower alkyl, lower alkoxy, halogen, hydroxy, methylenedioxy, trifluoromethyl, lower aleonoylamino, amino, di-lower alkylamino, carboxylic, carboxamido, carbo-lower alkoxy, alkylmercapto lower, lower alkylsulfinyl, lower alkylsulfonyl, nitro and sulfamollo, characterized by reacting a compound having formula III or V ** (See formula) ** wherein R6 and R7 have the meanings given above, with 2-amino-2-raethylpropionitrile or with an ammonia source and a cyanide ion source, or also in the case of reaction with the compound of formula IV, ** (See formula) ** with acetone-cyanhydrin, said reaction being carried out in the presence of an acid catalyst. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US346005A US3928380A (en) | 1973-03-29 | 1973-03-29 | 1,1{40 -Spirobis(cyclopenta-{8 4,5-c{9 pyrroles) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES447116A1 true ES447116A1 (en) | 1977-10-16 |
Family
ID=23357526
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES424717A Expired ES424717A1 (en) | 1973-03-29 | 1974-03-28 | Procedure for preparing carboxamides and thiocarboxamides. (Machine-translation by Google Translate, not legally binding) |
| ES447116A Expired ES447116A1 (en) | 1973-03-29 | 1976-04-15 | A procedure for preparing 2,4,5,6-tetrahidrociclopenta (c) pirrol-4-carbonitrilos. (Machine-translation by Google Translate, not legally binding) |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES424717A Expired ES424717A1 (en) | 1973-03-29 | 1974-03-28 | Procedure for preparing carboxamides and thiocarboxamides. (Machine-translation by Google Translate, not legally binding) |
Country Status (6)
| Country | Link |
|---|---|
| AR (1) | AR213064A1 (en) |
| ES (2) | ES424717A1 (en) |
| IE (1) | IE39694B1 (en) |
| IL (2) | IL44490A (en) |
| PH (1) | PH12366A (en) |
| SE (1) | SE7609982L (en) |
-
1974
- 1974-03-25 IL IL44490A patent/IL44490A/en unknown
- 1974-03-26 IE IE656/74A patent/IE39694B1/en unknown
- 1974-03-28 ES ES424717A patent/ES424717A1/en not_active Expired
- 1974-03-29 PH PH7415680A patent/PH12366A/en unknown
- 1974-03-29 AR AR253065A patent/AR213064A1/en active
-
1976
- 1976-04-15 ES ES447116A patent/ES447116A1/en not_active Expired
- 1976-08-11 IL IL50239A patent/IL50239A0/en unknown
- 1976-09-09 SE SE7609982A patent/SE7609982L/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE39694B1 (en) | 1978-12-06 |
| PH12366A (en) | 1979-01-29 |
| ES424717A1 (en) | 1976-11-01 |
| IL44490A (en) | 1978-09-29 |
| IL50239A0 (en) | 1976-10-31 |
| AR213064A1 (en) | 1978-12-15 |
| IE39694L (en) | 1974-09-29 |
| IL44490A0 (en) | 1974-06-30 |
| SE7609982L (en) | 1977-12-30 |
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