Claims
- 1. A process for the preparation of a compound of the formula ##STR14## wherein R.sup.1 and R.sup.2 independently are hydrogen, amino, OR.sup.5, OCOR.sup.6 or NHCOR.sup.5 wherein R.sup.5 is hydrogen or lower alkyl and R.sup.6 is lower alkyl or phenyl; R.sup.3 is lower alkyl; R.sup.4 is oxo, ##STR15## wherein R.sup.13 is lower alkyl, lower alkoxy-lower alkylene, tetrahydropyranyl or teytrahydrofuryl, R.sup.14 is lower alkyl or phenyl and R.sup.15 and R.sup.16 are lower alkyl or taken together form lower alkylene or arylene of 6 to 10 carbon atoms, and n is 1 or 2, which comprises the steps of
- a. condensing a compound of the formula ##STR16## wherein R.sup.3, R.sup.4 and n are as hereinbefore defined with a compound of the formula ##STR17## wherein R.sup.7 and R.sup.8 independently and respectively are R.sup.1 and R.sup.2, nitro, benzyloxy, dephenylmethoxy or triphenylmethoxy, and R.sup.9 is hydrogen, cyano or COOR.sup.10 wherein R.sup.10 is lower alkyl or benzyl, in the presence of a base to give a compound of the formula ##STR18## wherein R.sup.3, R.sup.4, R.sup.7, R.sup.8 and n are as hereinbefore defined;
- b. saponifying and then decarboxylating a compound obtained in step (a) when R.sup.9 is cyano or COOR.sup.10 wherein R.sup.10 is a hereinbefore defined in the presence of alkali and then in the presence of acid to give a compound of the formula ##STR19## wherein R.sup.3, R.sup.4, R.sup.7, R.sup.8 and n are as hereinbefore defined, and
- c. hydrogenating a compound obtained in step (b) in the presence of a noble metal or nickel catalyst.
- 2. The process according to claim 1 wherein the base of step (a) is present in a catalytic amount.
- 3. The process according to claim 2 wherein the catalytic amount is 1 to 10 mole percent.
- 4. The process of claim 1 wherein R.sup.3 is lower alkyl; R.sup.4 is ##STR20## wherein R.sup.13 is lower alkyl or lower alkoxy-lower alkylene; R.sup.7 is nitro or OR.sup.5 wherein R.sup.5 is lower alkyl; R.sup.8 is hydrogen or OR.sup.5 wherein R.sup.5 is lower alkyl; R.sup.9 is hydrogen and n is 1 or 2.
- 5. The process of claim 4 wherein R.sup.3 is methyl or ethyl; R.sup.13 is tert.-butyl or methoxymethylene, R.sup.5 is methyl; and n is 1.
- 6. A process for the preparation of a compound of the formula ##STR21## wherein R.sup.1 and R.sup.2 independently are hydrogen, amino, OR.sup.5, OCOR.sup.6 or NHCOR.sup.5 wherein R.sup.5 is hydrogen or lower alkyl and R.sup.6 is lower alkyl or phenyl; R.sup.3 is lower alkyl; R.sup.4 is oxo, ##STR22## wherein R.sub.13 is lower alkyl, lower alkoxy-lower alkylene, tetrahydropyranyl or tetrahydrofuryl, R.sup.14 is lower alkyl or phenyl and R.sup.15 and R.sup.16 are lower alkyl or taken together form lower alkylene or arylene of 6 to 10 carbon atoms, and n is 1 or 2,
- which comprises the steps of
- a. condensing a compound of the formula ##STR23## wherein R.sup.3 is lower alkyl; R.sup.4 is oxo, ##STR24## wherein R.sup.13 is lower alkyl, lower alkoxy-lower alkylne, tetrahydropyranyl or tetrahydrofuryl, R.sup.14 is lower alkyl or phenyl and R.sup.15 and R.sup.16 are lower alkyl or taken together form lower alkylene or arylene of 6 to 10 carbon atoms; X is OR.sup.11, N(R.sup.12).sub.2, SR.sup.11, N.sup.+(R.sup.12).sub.3, ##STR25## or S.sup.+(R.sup.12).sub.2 wherein R.sup.11 is hydrogen, lower alkyl, acetyl or benzoyl, R.sup.12 is lower alkyl, and m is 1 or 2; and n is 1 or 2,
- with a compound of the formula ##STR26## wherein R.sup.7 and R.sup.8 independently and respectively are R.sup.1 and R.sup.2, nitro, benzyloxy, diphenylmethoxy or triphenylmethoxy, and R.sup.9 is hydrogen, cyano or COOR.sup.10 wherein R.sup.10 is lower alkyl or benzyl,
- in the presence of a base to give a compound of the formula ##STR27## wherein R.sup.3, R.sup.4, R.sup.7, R.sup.8 and n are as hereinbefore defined;
- b. saponifying and then decarboxylating a compound obtained in step (a) when R.sup.9 is cyano or COOR.sup.10 wherein R.sup.10 is as hereinbefore defined in the presence of alkali and then in the presence of acid to give a compound of the formula ##STR28## wherein R.sup.3, R.sup.4, R.sup.7, R.sup.8, R.sup.9 and n are as hereinbefore defined, and
- c. hydrogenating a compound obtained in step (b) in the presence of a noble metal or nickel catalyst.
- 7. The process according to claim 6 wherein R.sup.3 is lower alkyl; R.sup.4 is ##STR29## wherein R.sup.13 is lower alkyl or lower alkoxy-lower alkylene; R.sup.7 is nitro or OR.sup.5 wherein R.sup.5 is lower alkyl; R.sup.8 is hydrogen or OR.sup.5 wherein R.sup.5 is lower alkyl; R.sup.9 is hydrogen and n is 1 or 2.
- 8. The process of claim 7 wherein R.sup.3 is methyl or ethyl; R.sup.13 is tert.-butyl or methoxymethylene, R.sup.5 is methyl; and n is 1.
Priority Claims (1)
Number |
Date |
Country |
Kind |
18029/73 |
Dec 1973 |
CH |
|
Parent Case Info
This is a division of application Ser. No. 533,101 filed Dec. 16, 1974, now abandoned.
US Referenced Citations (2)
Number |
Name |
Date |
Kind |
3929876 |
Hajos |
Dec 1975 |
|
4008253 |
Souer et al. |
Feb 1977 |
|
Foreign Referenced Citations (1)
Number |
Date |
Country |
7,217,629 |
Jun 1973 |
NL |
Non-Patent Literature Citations (1)
Entry |
Hunig et al., as cited in C.A. 50, 14599(f) (1956). |
Divisions (1)
|
Number |
Date |
Country |
Parent |
533101 |
Dec 1974 |
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