CA1180326A - 1,4-dioxaspiro[4,5]decene compounds - Google Patents
1,4-dioxaspiro[4,5]decene compoundsInfo
- Publication number
- CA1180326A CA1180326A CA000407793A CA407793A CA1180326A CA 1180326 A CA1180326 A CA 1180326A CA 000407793 A CA000407793 A CA 000407793A CA 407793 A CA407793 A CA 407793A CA 1180326 A CA1180326 A CA 1180326A
- Authority
- CA
- Canada
- Prior art keywords
- halogen
- acylamino
- aromatization
- carried out
- substituted
- 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
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
?4-DIOXASPIRO[4,5] DECENE COMPOUNDS
ABSTRACT OF THE DISCLOSURE
A process for preparing 3-substituted-2-hydroxypropyl aryl ether .beta.-blockers of the formula;
wherein Y is halogen, hydroxy, lower acyloxy, amino, lower alkylamino, lower aralkylamino, lower acylamino, di-lower alkylamino, lower alkyleneamino, N-lower alkyl-N-lower aralkylamino, di-lower acylamino, N-lower aklyl-N-lower acylamino or N-tri-lower alkylsilylamino; one of P and R combined together with Q shows lower alkylene or alkenylene optionally interrupted by O, N or S and optionally substituted by lower alkyl, lower araklyl, lower carboxylic acyl, carboxy, protected carboxy;
hydroxy, lower alkoxy, lower acyloxy, oxo; amino, lower alkylamino, lower acylamino, nitro, nitroso, lower alkylthio, lower sulfonic acyl or halogen; and remaining R and P is hydrogen or halogen which comprises aromatizing a 2-(substituted methyl) -1,4,dioxaspiro[4,5]-decene compound of the formula:
ABSTRACT OF THE DISCLOSURE
A process for preparing 3-substituted-2-hydroxypropyl aryl ether .beta.-blockers of the formula;
wherein Y is halogen, hydroxy, lower acyloxy, amino, lower alkylamino, lower aralkylamino, lower acylamino, di-lower alkylamino, lower alkyleneamino, N-lower alkyl-N-lower aralkylamino, di-lower acylamino, N-lower aklyl-N-lower acylamino or N-tri-lower alkylsilylamino; one of P and R combined together with Q shows lower alkylene or alkenylene optionally interrupted by O, N or S and optionally substituted by lower alkyl, lower araklyl, lower carboxylic acyl, carboxy, protected carboxy;
hydroxy, lower alkoxy, lower acyloxy, oxo; amino, lower alkylamino, lower acylamino, nitro, nitroso, lower alkylthio, lower sulfonic acyl or halogen; and remaining R and P is hydrogen or halogen which comprises aromatizing a 2-(substituted methyl) -1,4,dioxaspiro[4,5]-decene compound of the formula:
Claims (11)
PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A process for preparing 2-hydroxy-3-substituted-propyl aryl ethers represented by the following formula:
wherein Y is halogen, hydroxy, lower acyloxy, amino, lower alkylamino, lower aralkylamino, lower acylamino, di-lower alkylamino, lower alkyleneamino, N-lower alkyl-N-lower aralkylamino, di-lower acylamino, N-lower alkyl-N-lower acylamino or N-tri-lower alkylsilylamino; one of P and R combined togther with Q shows lower alkylene or alkenylene optionally interrupted by O, N or S and optionally substituted by lower alkyl, lower aralkyl, lower carboxylic acyl, carboxy, protected carboxy, hydroxy, lower alkoxy, lower acyloxy, oxo; amino, lower alkylamino, lower acylamino, nitro, nitroso, lower alkylthio, lower sulfonic acyl or halogen; and remining R and P is hydrogen or halogen; which comprises aromatizing a 2-(substituted methyl)-1,4-dioxaspiro[4,5]-decene compound presented by the following formula:
wherein Y, P, Q, and R are as defined above, X is hydrogen or halogen and the dotted line represents, if X is hydrogen, two double bonds or if X is halogen represents a double dond, wherein the aromatization is carried out by the action of a base, adsorbing agent, metal salt or heating.
wherein Y is halogen, hydroxy, lower acyloxy, amino, lower alkylamino, lower aralkylamino, lower acylamino, di-lower alkylamino, lower alkyleneamino, N-lower alkyl-N-lower aralkylamino, di-lower acylamino, N-lower alkyl-N-lower acylamino or N-tri-lower alkylsilylamino; one of P and R combined togther with Q shows lower alkylene or alkenylene optionally interrupted by O, N or S and optionally substituted by lower alkyl, lower aralkyl, lower carboxylic acyl, carboxy, protected carboxy, hydroxy, lower alkoxy, lower acyloxy, oxo; amino, lower alkylamino, lower acylamino, nitro, nitroso, lower alkylthio, lower sulfonic acyl or halogen; and remining R and P is hydrogen or halogen; which comprises aromatizing a 2-(substituted methyl)-1,4-dioxaspiro[4,5]-decene compound presented by the following formula:
wherein Y, P, Q, and R are as defined above, X is hydrogen or halogen and the dotted line represents, if X is hydrogen, two double bonds or if X is halogen represents a double dond, wherein the aromatization is carried out by the action of a base, adsorbing agent, metal salt or heating.
2. A process of claim 1, wherein the aromatization is carried out by the reaction of a secondary amine.
3. A process of claim 1, wherein the secondary amine is morpholine or piperidine and the reaction is carried out at 80 degress C to 150 degrees C.
4. A process of claim 1, wherein the aromatization is carried out by the action of a Lewis acid.
5. A process of claim 4, wherein the Lewis acid is one selected from stannic chloride, boron trichloride and titanium tetrachloride.
6. A process of claim 4, wherein the aromatization is carried out in the presence of a tertiary amine.
7. A process of claim 6, wherein the tertiary amine is triethylamine, tributylamine, trioctylamine, quinuclidine or 1,4-diazabicylco[2,2,2]octane.
8. A process of claim 4, wherein Y is lower alkylamino or lower alkyleneamino.
9. A process of claim 1, wherein the aromatization is carried out by the action of a mineral acid or adsorbent.
10. A process of claim 1, wherein the starting 2-(substituted methyl)-1,4-dioxaspiro is prepared by treating a cyclohexenone compound of the following formula:
wherein P, Q, X, R and the dotted line are as defined in claim 1 or its reactive derivative with a 3-substituted-propyleneglycol compound of the following formula:
wherein Y is as defined in claim 1, or its reactive derivative in an inert solvent optionally in the presence of an acid catalyst for condensation at a temperature of range from -50 degrees C to 150 degrees C.
wherein P, Q, X, R and the dotted line are as defined in claim 1 or its reactive derivative with a 3-substituted-propyleneglycol compound of the following formula:
wherein Y is as defined in claim 1, or its reactive derivative in an inert solvent optionally in the presence of an acid catalyst for condensation at a temperature of range from -50 degrees C to 150 degrees C.
11. A process of claim 10, wherein said starting compound as prepared in a reaction medium is subjected in the same reaction medium to said subsequent aromatization step to prepare the final product.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000407793A CA1180326A (en) | 1979-03-07 | 1982-07-21 | 1,4-dioxaspiro[4,5]decene compounds |
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2701079A JPS55118432A (en) | 1979-03-07 | 1979-03-07 | 2-spipo-1,3-dioxolane compound and new synthesis of aromatic ether by its ring opening reaction |
| JP27010/1979 | 1979-03-07 | ||
| JP10399/1980 | 1980-01-30 | ||
| JP1039980A JPS56108764A (en) | 1980-01-30 | 1980-01-30 | Novel synthesis of beta-blocker |
| CA000346987A CA1139760A (en) | 1979-03-07 | 1980-03-04 | 1,4-dioxaspiro¬4,5| decene compounds |
| CA000407793A CA1180326A (en) | 1979-03-07 | 1982-07-21 | 1,4-dioxaspiro[4,5]decene compounds |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000346987A Division CA1139760A (en) | 1979-03-07 | 1980-03-04 | 1,4-dioxaspiro¬4,5| decene compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1180326A true CA1180326A (en) | 1985-01-02 |
Family
ID=27426222
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000407793A Expired CA1180326A (en) | 1979-03-07 | 1982-07-21 | 1,4-dioxaspiro[4,5]decene compounds |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1180326A (en) |
-
1982
- 1982-07-21 CA CA000407793A patent/CA1180326A/en not_active Expired
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Kupchan et al. | Isolation and structural elucidation of allamandin, and antileukemic iridoid lactone from Allamanda cathartica | |
| HUP9904275A2 (en) | Processes and intermediates for preparing 1-benzyl-4-(5,6-dimethoxy-1-indanon)-2-yl)methylpiperidine | |
| Shevaldina et al. | One‐pot acid‐free ferrocenylalkylation of azoles with α‐ferrocenyl alcohols: ferrocene‐based plant growth regulators and herbicide safeners | |
| Matteson | Cycloaddition of Diazo Compounds to Ethyleneboronic and Acetyleneboronio Esters1 | |
| CA1180326A (en) | 1,4-dioxaspiro[4,5]decene compounds | |
| GB1461173A (en) | Preparation of 3- 4-or 5-substituted thiazol-2-oxy- propanediol 1,2-acetonides | |
| Cunico et al. | Synthesis of oxazoles from O-trimethylsilyl acyltrimethylsilane cyanohydrins | |
| JPH01261377A (en) | Substituted pyrimidine | |
| IE781155L (en) | Thienotetrahydropyridines | |
| JPS54100367A (en) | 5-phenethyl-2-oxazolidone derivative and its preparation | |
| US3956388A (en) | N-methylol ethers of glycollic anilides | |
| US2192840A (en) | Method of preparing quinuclidine and derivatives thereof | |
| GB758382A (en) | Improvements in bis-(ú-aminophenoxy) alkane derivatives | |
| US2464260A (en) | Quaternary ammonium halides of benzhydryl ether derivatives | |
| KR830001958A (en) | Method for producing 2-hydroxy-3-substituted-propyl aryl ethers | |
| Beckett et al. | Trialkylsilyl moieties as potential pharmacokinetic modifying groups for aminoalcohols | |
| IL58828A (en) | 3-bromoisoxazole derivatives,the preparation of 1-(3-bromoisoxazol-5-yl)-2-tert.butylaminoethanol and pharmaceutical compositions containing it | |
| JPS56156263A (en) | Carbostyril derivative | |
| EP0001290B1 (en) | Substituted 2,3-dihydrobenz-(d)-isothiazole-1,1-dioxides and 2,3-dihydronaphtho-(1,8-de)-1,2-thiazine-1,1-dioxides | |
| Bozak et al. | Synthesis and Crystal Structure of 1-Ethoxyferrocenylmethyl-3-ferrocenylmethylene-1-cyclohexene, C~ 3~ 0H~ 3~ 2OFe~ 2 | |
| JPS6150943A (en) | Manufacture of organic compound having alkoxyalkylidene group | |
| ES434089A1 (en) | D-glucose-1-0-nicotinoyl-2-deoxy-2-nictinamido derivatives | |
| US3140310A (en) | Nu, nu'-di (lower alkenyl) bicarbamate esters | |
| JPS55129268A (en) | Carbostyril derivative | |
| Zheng et al. | Stereoselective Preparation of (Z)-γ-Silyl-γ, δ-Unsaturated Ketones and their Application in the Synthesis of 1, 4-Diketones |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |