Claims
- 1. A process for the manufacture of 1,4-dicyano-substituted bicyclic or tricyclic compounds of formula ##STR57## wherein R.sub.1 represents hydrogen, halogen, alkyl, alkoxy, carboxy, carbalkoxy, --CONR.sub.5 R.sub.6, wherein each of R.sub.5 and R.sub.6 independently represents hydrogen or alkyl, or together they complete a 5- or 6-membered heterocyclic ring, sulpho-, --SO.sub.2 NR.sub.5 R.sub.6, in which R.sub.5 and R.sub.6 are as defined hereinbefore, alkylsulphonyl, arylsulphonyl, cyano, nitro, or together with R.sub.2 completes a 6-membered aromatic ring or represents the methylenedioxy radical, R.sub.2 represents hydrogen, halogen, alkyl, alkoxy, carboxy, carbalkoxy, --CONR.sub.5 R.sub.6, wherein R.sub.5 and R.sub.6 are as defined hereinbefore, alkylsulphonyl, nitro, or together with R.sub.1 completes a 6-membered aromatic ring or represents the methylenedioxy radical, R.sub.3 represents hydrogen, halogen or alkyl and R.sub.4 represents hydrogen, halogen or alkyl, which process comprises reacting an o-xylene dicyanide of formua ##STR58## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined hereinbefore, with glyoxal, in the presence of a base and a solvent, at temperatures below 50.degree. C.
- 2. A process according to claim 1 for the manufacture of 1,4dicyano-substituted bicyclic or tricyclic compounds of formula ##STR59## wherein R.sub.1 ' represents hydrogen, halogen, alkyl, alkoxy, carboxy, carbalkoxy, --CONR.sub.5 R.sub.6, wherein each of R.sub.5 and R.sub.6 independently represents hydrogen or alkyl, or together they complete a 5- or 6-membered heterocyclic ring, alkyl-sulphonyl, arylsulphonyl, cyano, nitro, or together with R.sub.2 ' completes a 6-membered aromatic ring or represents the methylenedioxy radical, R.sub.2 ' represents hydrogen, halogen, alkyl, alkoxy, alkylsulphonyl, or together with R.sub.1 ' completes a 6-membered aromatic ring or represents the methylenedioxy radical, and R.sub.3 and R.sub.4 are as defined in claim 1, which process comprises reacting an o-xylene dicyanide of formula ##STR60## wherein R.sub.1 ', R.sub.2 ', R.sub.3 and R.sub.4 are as defined hereinbefore, with glyoxal.
- 3. A process according to claim 1 for the manufacture of 1,4-dicyano-substituted bicyclic or tricyclic compounds of formula ##STR61## wherein R.sub.1 " represents hydrogen, halogen, alkyl, alkylsulphonyl, arylsulphonyl, or together with R.sub.2 " completes a 6-membered aromatic ring, R.sub.2 " represents hydrogen, halogen, alkyl, alkylsulphonyl, or together with R.sub.1 " completes a 6-membered aromatic ring, R.sub.3 represents hydrogen, halogen or alkyl, and R.sub.4 represents hydrogen, halogen or alkyl, which process comprises reacting an o-xylylene dicyanide of formula ##STR62## wherein R.sub.1 ", R.sub.2 ", R.sub.3 and R.sub.4 are as defined hereinbefore, with glyoxal.
- 4. A process according to claim 1 for the manufacture of 1,4-dicyano-substituted bicyclic or tricyclic compounds of formula ##STR63## wherein R.sub.1 "' represents hydrogen, halogen or alkyl, or together with R.sub.2 "' completes a 6-membered aromatic ring, R.sub.2 "' represents hydrogen, halogen or alkyl, or together with R.sub.1 "' completes a 6-membered aromatic ring, R.sub.3 ' represents hydrogen or halogen and R.sub.4 ' represents hydrogen or halogen, which process comprises reacting an o-xylylene dicyanide of formula ##STR64## wherein R.sub.1 "' , R.sub.2 "', R.sub.3 ' and R.sub.4 ' are as defined hereinbefore, with glyoxal.
- 5. A process according to claim 1 for the manufacture of 1,4-dicyano-substituted naphthalenes of formula ##STR65## wherein R.sub.1 "" represents hydrogen, halogen or alkyl, R.sub.2 ""represents hydrogen, halogen or alkyl, and R.sub.3 ' represents hydrogen or halogen, which process comprises reacting an o-xylylene dicyanide of formula ##STR66## wherein R.sub.1 "", R.sub.2 "", and R.sub.3 ' are as defined hereinbefore, with glyoxal.
- 6. A process according to claim 1 for the manufacture of 1,4-dicyano-substituted naphthalenes of formula ##STR67## wherein R.sub.1.sup.V represents hydrogen or halogen and R.sub.3 ' represents hydrogen or halogen, which comprises reacting an o-xylylene dicyanide of formula ##STR68## wherein R.sub.1.sup.V and R.sub.3 ' are as defined hereinbefore, with glyoxal.
- 7. A process according to claim 1 for the manufacture of 1,4-dicyanonaphthalene of formula ##STR69## which comprises reacting o-xylylene dicyanide of formula ##STR70## with glyoxal.
Priority Claims (2)
Number |
Date |
Country |
Kind |
15190/74 |
Nov 1974 |
CH |
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15191/74 |
Nov 1974 |
CH |
|
Parent Case Info
This is a division of application Ser. No. 629,180, filed on Nov. 5, 1975, now U.S. Pat. No. 4,011,261.
Non-Patent Literature Citations (1)
Entry |
dvornikoff: Chemical Abstracts, vol. 44, p. 10740. |
Divisions (1)
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Number |
Date |
Country |
Parent |
629180 |
Nov 1975 |
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