GB1121924A - Process for the preparation of bicyclic amidines - Google Patents
Process for the preparation of bicyclic amidinesInfo
- Publication number
- GB1121924A GB1121924A GB3960866A GB3960866A GB1121924A GB 1121924 A GB1121924 A GB 1121924A GB 3960866 A GB3960866 A GB 3960866A GB 3960866 A GB3960866 A GB 3960866A GB 1121924 A GB1121924 A GB 1121924A
- Authority
- GB
- United Kingdom
- Prior art keywords
- preparation
- pyrimidine
- pyrrolo
- hexahydro
- integer
- 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
- 238000002360 preparation method Methods 0.000 title abstract 3
- -1 bicyclic amidines Chemical class 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 abstract 2
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 abstract 1
- HWGJWYNMDPTGTD-UHFFFAOYSA-N 1h-azonine Chemical compound C=1C=CC=CNC=CC=1 HWGJWYNMDPTGTD-UHFFFAOYSA-N 0.000 abstract 1
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 abstract 1
- VCDGIIXLUSKSCX-UHFFFAOYSA-N 3,4,5,7,8,9-hexahydro-2h-pyrrolo[1,2-a][1,3]diazepine Chemical compound C1CCCN=C2CCCN21 VCDGIIXLUSKSCX-UHFFFAOYSA-N 0.000 abstract 1
- NGENSVOAXQDAGA-UHFFFAOYSA-N 3,5,6,7-tetrahydro-2h-pyrrolo[1,2-a]imidazole Chemical compound C1CN=C2CCCN21 NGENSVOAXQDAGA-UHFFFAOYSA-N 0.000 abstract 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 abstract 1
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 235000019270 ammonium chloride Nutrition 0.000 abstract 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 abstract 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 abstract 1
- 239000001166 ammonium sulphate Substances 0.000 abstract 1
- 235000011130 ammonium sulphate Nutrition 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 230000008030 elimination Effects 0.000 abstract 1
- 238000003379 elimination reaction Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 235000011167 hydrochloric acid Nutrition 0.000 abstract 1
- 235000011007 phosphoric acid Nutrition 0.000 abstract 1
- 150000003016 phosphoric acids Chemical class 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 abstract 1
- PMZURENOXWZQFD-UHFFFAOYSA-L sodium sulphate Substances [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
A process for the preparation of bicyclic amidines of the formula <FORM:1121924/C2/1> in which m is an integer from 3 to 7 and n is an integer from 2 to 4 comprises heating N-(amino-alkyl)-lactams of the formula <FORM:1121924/C2/2> in which m and n have the meaning given above at an elevated temperature in the presence of an acid catalyst to effect cyclization and elimination of water. Catalysts specified include hydrochloric, sulphuric and phosphoric acids, p-toluene-sulphonic acid, sodium hydrogen sulphate, ammonium chloride or ammonium sulphate. Examples relate to the preparation of 2,3,5,6 - tetrahydro - 7H - pyrrolo [1,2-a] imidazole; 2,3,4,6,7,8 - hexahydropyrrolo [1,2-a] pyrimidine; 2,3,4,5,7,8 - hexahydro-9H-pyrrolo [1,2-a] [1,3] diazepine; 3,4,6,7,8,9-hexahydro - 2H - pyrrido - [1,2-a] pyrimidine; 2,3,4,6,7,8,9,10 - octahydropyrimidino-[1,2-a] azepine and 2,3,4,6,7,8,9,10,11,12 - decahydro-pyrimidine-[1,2-a] azonine.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0047138 | 1965-09-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1121924A true GB1121924A (en) | 1968-07-31 |
Family
ID=7101441
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3960866A Expired GB1121924A (en) | 1965-09-09 | 1966-09-05 | Process for the preparation of bicyclic amidines |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE686571A (en) |
| CH (1) | CH471804A (en) |
| GB (1) | GB1121924A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3976645A (en) * | 1973-12-20 | 1976-08-24 | John Wyeth & Brother Limited | Process for the preparation of 10-(halophenyl)-2,3,4,10-tetrahydropyrimido-[1,2-a]indol-10-ol |
| US4226972A (en) * | 1978-11-03 | 1980-10-07 | The Firestone Tire & Rubber Company | Process for preparing poly(organophosphazenes) from soluble or gelled poly(dichlorophosphazenes) |
| US4943633A (en) * | 1988-06-22 | 1990-07-24 | Air Products And Chemicals, Inc. | Catalytic preparation of cyanoalkyl lactams |
| US5723605A (en) * | 1993-11-11 | 1998-03-03 | Lonza Ltd. | Bicyclic amidines, process for their preparation, and their use as catalyst |
| US9085712B2 (en) | 2013-03-14 | 2015-07-21 | Bayer Materialscience Llc | Fast cure aspartate polysiloxane hybrid coating |
| US20180148601A1 (en) * | 2016-11-30 | 2018-05-31 | Momentive Performance Materials Inc. | Abrasion resistant coating composition with inorganic metal oxides |
-
1966
- 1966-08-11 CH CH1159766A patent/CH471804A/en not_active IP Right Cessation
- 1966-09-05 GB GB3960866A patent/GB1121924A/en not_active Expired
- 1966-09-07 BE BE686571D patent/BE686571A/xx unknown
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3976645A (en) * | 1973-12-20 | 1976-08-24 | John Wyeth & Brother Limited | Process for the preparation of 10-(halophenyl)-2,3,4,10-tetrahydropyrimido-[1,2-a]indol-10-ol |
| US4226972A (en) * | 1978-11-03 | 1980-10-07 | The Firestone Tire & Rubber Company | Process for preparing poly(organophosphazenes) from soluble or gelled poly(dichlorophosphazenes) |
| US4943633A (en) * | 1988-06-22 | 1990-07-24 | Air Products And Chemicals, Inc. | Catalytic preparation of cyanoalkyl lactams |
| US5723605A (en) * | 1993-11-11 | 1998-03-03 | Lonza Ltd. | Bicyclic amidines, process for their preparation, and their use as catalyst |
| US5922869A (en) * | 1993-11-11 | 1999-07-13 | Lonza Ltd. | Bicyclic amidines, process for their preparation, and their use as catalyst |
| US6255488B1 (en) | 1993-11-11 | 2001-07-03 | Lonza Ag | Bicyclic amidines, process for their preparation, and their use as catalyst |
| US6476175B2 (en) | 1993-11-11 | 2002-11-05 | Lonza Ltd. | Bicyclic amidines, process for their preparation, and their use as catalyst |
| US9085712B2 (en) | 2013-03-14 | 2015-07-21 | Bayer Materialscience Llc | Fast cure aspartate polysiloxane hybrid coating |
| US9957417B2 (en) | 2013-03-14 | 2018-05-01 | Covestro Llc | Fast cure aspartate polysiloxane hybrid coating |
| US20180148601A1 (en) * | 2016-11-30 | 2018-05-31 | Momentive Performance Materials Inc. | Abrasion resistant coating composition with inorganic metal oxides |
Also Published As
| Publication number | Publication date |
|---|---|
| BE686571A (en) | 1967-03-07 |
| DE1545855A1 (en) | 1970-02-05 |
| CH471804A (en) | 1969-04-30 |
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