GB791805A - Improvements in or relating to substituted indoles, intermediates therefor, and process for preparing the same - Google Patents
Improvements in or relating to substituted indoles, intermediates therefor, and process for preparing the sameInfo
- Publication number
- GB791805A GB791805A GB999355A GB999355A GB791805A GB 791805 A GB791805 A GB 791805A GB 999355 A GB999355 A GB 999355A GB 999355 A GB999355 A GB 999355A GB 791805 A GB791805 A GB 791805A
- Authority
- GB
- United Kingdom
- Prior art keywords
- benzoyl
- hydroxy
- alkyl
- keto
- acyl
- 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
- 150000002475 indoles Chemical class 0.000 title 1
- 239000000543 intermediate Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 polymethylene chain Polymers 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 abstract 2
- 239000004593 Epoxy Substances 0.000 abstract 2
- 229930194542 Keto Natural products 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 150000003840 hydrochlorides Chemical class 0.000 abstract 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 abstract 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- HIYWOHBEPVGIQN-UHFFFAOYSA-N 1h-benzo[g]indole Chemical class C1=CC=CC2=C(NC=C3)C3=CC=C21 HIYWOHBEPVGIQN-UHFFFAOYSA-N 0.000 abstract 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 238000006735 epoxidation reaction Methods 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- 150000002689 maleic acids Chemical class 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003016 phosphoric acids Chemical class 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 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
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/90—Benzo [c, d] indoles; Hydrogenated benzo [c, d] indoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Benz-indoles of the formul : <FORM:0791805/IV (b)/1> <FORM:0791805/IV (b)/2> <FORM:0791805/IV (b)/3> in which R is alkyl (C1-C8), monocyclic aryl (which may be substituted by C1-C7 alkyl) or monocyclic aralkyl (having 1-7 carbon atoms in the alkyl portion), R1 is C1-C8 alkyl, and R2 and R3 and C1-C7 alkyl or together for a polymethylene chain of 2-3 carbon atoms, are prepared as follows: A 1-acyl-5-ketohexahydro-benzindole of the formula: <FORM:0791805/IV (b)/4> (prepared by ring-closure of a 1-acyl-indoline-3-propionyl chloride) is reduced with alkali borohydride to the 5-hydroxy compound, the hydroxyl replaced by halogen with a phosphorus trihalide or hydrobromic acid, a double bond introduced into the 4 : 5-position by heating with a high-boiling tertiary amine, and epoxidation effected; two alternative routes are now possible: (1) heating with R1NH2 gives the 4-alkylamino-5-hydroxy compound which is condensed with a haloacetone to form the N-alkyl-N-acetonyl derivative; the 5-hydroxy group is oxidized to keto (e.g. with manganese dioxide) and if desired the N-acyl group is hydrolysed with strong acid; (2) the 4 : 5-epoxy compound is condensed with an alkylamino-acetone ketal and the 5-hydroxy group then oxidized as in (1); optional treatment with strong acid hydrolysis the N-acyl and ketal groups simultaneously. In the examples the following substituted 1 : 2 : 2a : 3 : 4 : 5-hexahydro - benz - [cd] - indoles are prepared: 1 - benzoyl - 5 - keto, 1 - benzoyl - 5 - hydroxy, 1 - benzoyl - 5 - bromo, 1 - benzoyl - 5 - chloro, 1 - benzoyl - 4 : 5 - dehydro, 1 - benzoyl - 4 : 5-epoxy, 1 - benzoyl - 4 - methylamino - 5 - hydroxy, 1 - benzoyl - 4 - (N - methyl - N - acetonylamino) - 5 - hydroxy and its ethylene ketal (and hydrochlorides) the corresponding 5-keto compounds (and hydrochlorides), also anaolgous compounds with a 1-acetyl group, and finally the 5-keto-4-(N-methyl-N-acetonylamino) compound without the 1-substituent. It is stated that R may also be ethyl, amyl, hexyl, benzyl or p-ethylphenyl, R1 may be ethyl, isopropyl, butyl, amyl or heptyl and R2 and R3 may be propylene, diethyl or dipropyl. The amino compounds form salts also with hydrobromic, acetic, propionic, sulphuric, phosphoric and maleic acids. Reference has been directed by the Comptroller to Specifications 745,495 and 774,986.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB990255A GB791804A (en) | 1955-04-05 | 1955-04-05 | Improvements in or relating to substituted benz-indoles, intermediates therefor, andprocess for preparing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB791805A true GB791805A (en) | 1958-03-12 |
Family
ID=9880909
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB999355A Expired GB791805A (en) | 1955-04-05 | 1955-04-05 | Improvements in or relating to substituted indoles, intermediates therefor, and process for preparing the same |
| GB990255A Expired GB791804A (en) | 1955-04-05 | 1955-04-05 | Improvements in or relating to substituted benz-indoles, intermediates therefor, andprocess for preparing the same |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB990255A Expired GB791804A (en) | 1955-04-05 | 1955-04-05 | Improvements in or relating to substituted benz-indoles, intermediates therefor, andprocess for preparing the same |
Country Status (1)
| Country | Link |
|---|---|
| GB (2) | GB791805A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5212319A (en) * | 1990-02-26 | 1993-05-18 | Eli Lilly And Company | Intermediates to 4-amino-hexahydrobenz[cd]indoles and processes therefor |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5498727A (en) * | 1994-07-19 | 1996-03-12 | Agouron Pharmaceuticals, Inc. | Preparation of benzindole compounds from naphthalene compounds |
-
1955
- 1955-04-05 GB GB999355A patent/GB791805A/en not_active Expired
- 1955-04-05 GB GB990255A patent/GB791804A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5212319A (en) * | 1990-02-26 | 1993-05-18 | Eli Lilly And Company | Intermediates to 4-amino-hexahydrobenz[cd]indoles and processes therefor |
Also Published As
| Publication number | Publication date |
|---|---|
| GB791804A (en) | 1958-03-12 |
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