RO87060B - Process for the preparation of 5-hydroxy-3, 4-dihydro-2h-benzopyran derivatives - Google Patents
Process for the preparation of 5-hydroxy-3, 4-dihydro-2h-benzopyran derivativesInfo
- Publication number
- RO87060B RO87060B RO110333A RO11033383A RO87060B RO 87060 B RO87060 B RO 87060B RO 110333 A RO110333 A RO 110333A RO 11033383 A RO11033383 A RO 11033383A RO 87060 B RO87060 B RO 87060B
- Authority
- RO
- Romania
- Prior art keywords
- formula
- dihydro
- hydroxy
- preparation
- benzopyran derivatives
- Prior art date
Links
- IRSRNOYNZSCIBG-UHFFFAOYSA-N 3,4-dihydro-2h-chromen-5-ol Chemical class O1CCCC2=C1C=CC=C2O IRSRNOYNZSCIBG-UHFFFAOYSA-N 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyrane Compounds (AREA)
Abstract
Inventia se refera la un procedeu pentru prepararea unro derivati de 5-hidroxi-3,4-dihidro-2H-benzopiran cu formula generala I: (vezi formula) în care Q este o grupa NHCOR, NHCONH2, NHAr, NHOH, NR2R3CN sau CH2CO2H5 în care R1 este o grupare alchil cu 1...4 atomi de carbon, fenil sau feniletil, Ar reprezinta un radical: (vezi formula) în care R4 este un hidrogen sau metil, R2 si R3 reprezinta fiecare hidrogen sau un radical alchil cu 1...4 atomi de carbon, caracterizat prin aceea ca un compus cu formula II: (vezi formula) reactioneaza cu un compus cu formula III a sau III b: (vezi formula) în care Q are semnificatiile susmentionate iar Met reprezinta Na, K sau Li, la o temperatura cuprinsa între 20...160 degree C, în mediu de solvent ales dintre tetrahidrofuran sau piridina, formîndu-se un produs intermediar cu formula generala IV: (vezi formula) în care Q are semnificatiile susmentionate, care se supune debenzilarii prin hidrigenoliza în prezenta de catalizator de Pd/C, la presiune atmosferica.The invention relates to a process for the preparation of 5-hydroxy-3,4-dihydro-2H-benzopyran derivatives of the general formula I wherein Q is a group NHCOR, NHCONH2, NHAr, NHOH, NR2R3CN or CH2CO2H5 wherein R 1 is a C 1-4 alkyl group, phenyl or phenylethyl group, Ar is a radical: wherein R 4 is hydrogen or methyl, R 2 and R 3 are each hydrogen or an alkyl radical of 1 to 4 carbon atoms, characterized in that a compound of formula II: (see formula) is reacted with a compound of formula IIIa or IIIb: wherein Q is as defined above and Met is Na, K or Li at a temperature in the range of 20-160 ° C in a solvent medium chosen from tetrahydrofuran or pyridine to form an intermediate of general formula IV wherein Q has the abovementioned meanings, is debenzylated by hydrogenolysis in the presence of a Pd / C catalyst at pre atmospheric air.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/457,171 US4486428A (en) | 1982-03-16 | 1983-01-13 | Bicyclic benzo fused compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RO87060A RO87060A (en) | 1985-08-31 |
| RO87060B true RO87060B (en) | 1985-08-31 |
Family
ID=23815721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RO110333A RO87060B (en) | 1983-01-13 | 1983-03-15 | Process for the preparation of 5-hydroxy-3, 4-dihydro-2h-benzopyran derivatives |
Country Status (3)
| Country | Link |
|---|---|
| CS (1) | CS249127B2 (en) |
| PL (1) | PL140273B1 (en) |
| RO (1) | RO87060B (en) |
-
1983
- 1983-03-15 PL PL24102583A patent/PL140273B1/en unknown
- 1983-03-15 RO RO110333A patent/RO87060B/en unknown
- 1983-03-16 CS CS182383A patent/CS249127B2/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RO87060A (en) | 1985-08-31 |
| CS249127B2 (en) | 1987-03-12 |
| PL140273B1 (en) | 1987-04-30 |
| PL241025A1 (en) | 1985-04-09 |
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