# US 4,395,550 A · Tetrahydro-2(1H)-quinazolinones and cyclohexene nitriles

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- Number: US 4,395,550 A
- Document ID: US4395550A
- Status: Granted
- Kind: A
- Application number: 06/318,480
- Filed: 1981-11-05
- Granted: 1983-07-26
- Earliest claimed: 1979-07-05
- Assignees: Sandoz Ltd.
- Inventors: Peter Funfschilling
- Web page: https://patentgrep.com/patent/US4395550A

## CPC

- C07D 239/96: Two oxygen atoms
- C07D 239/82: with an aryl radical attached in position 4
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

A process for the production of 4-phenyl-2(1H)-quinazolinones and -4a,5,6,8a-tetrahydro-2(1H)-quinazolinones which comprises introducing the desired phenyl radical into a corresponding quinazolin-2,4(1H,3H)-dione by way of a Grignard reaction and hydrolysis of the resulting product.

## Claims

### Claim 1

A compound of the formula: ##STR10## wherein R.sub.1 is C.sub.1 -C.sub.5 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -cycloalkyl-(C.sub.1 -C.sub.4)-alkyl, C.sub.1 -C.sub.5 -haloalkyl, allyl or propargyl,
R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are independently of each other hydrogen, fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, nitro or trifluoromethyl, whereby at least two of R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are hydrogen, and
Y.sub.1 and Y.sub.2 are independently of each other hydrogen, fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or trifluoromethyl.

### Claim 2 (depends on 1)

A compound of claim 1 in which Y.sub.1 is hydrogen or fluoro and Y.sub.2 is hydrogen and R.sub.1 is isopropyl, 2,2,2-trifluoroethyl or cyclopropylmethyl.

### Claim 3 (depends on 2)

A compound of claim 2 in which R.sub.1 is isopropyl, R.sub.4 is methyl and R.sub.2, R.sub.3 and R.sub.5 are each hydrogen.

### Claim 4

A compound of the formula: ##STR11## wherein R.sub.1 is C.sub.1 -C.sub.5 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -cycloalkyl-(C.sub.1 -C.sub.4)-alkyl, C.sub.1 -C.sub.5 -haloalkyl, allyl or propargyl, and
R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are independently of each other hydrogen, fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, nitro or trifluoromethyl, whereby at least two of R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are hydrogen.

### Claim 5 (depends on 4)

A compound of claim 4 in which R.sub.1 is isopropyl, 2,2,2-trifluoroethyl or cyclopropylmethyl.

### Claim 6 (depends on 5)

A compound of claim 5 in which R.sub.1 is isopropyl, R.sub.4 is methyl and R.sub.2, R.sub.3 and R.sub.5 are each hydrogen.

### Claim 7

A compound of the formula: ##STR12## wherein R is C.sub.1 -C.sub.4 -alkyl,
R.sub.1 is C.sub.1 -C.sub.5 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -cycloalkyl-(C.sub.1 -C.sub.4)-alkyl, C.sub.1 -C.sub.5 -haloalkyl, allyl or propargyl, and
R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are independently of each other hydrogen, fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, nitro or trifluoromethyl, whereby at least two of R.sub.2,
R.sub.3, R.sub.4 and R.sub.5 are hydrogen.

### Claim 8 (depends on 7)

A compound of claim 7 in which R.sub.1 is isopropyl, 2,2,2-trifluoromethyl or cyclopropylmethyl.

### Claim 9 (depends on 8)

A compound of claim 8 in which R.sub.1 is isopropyl, R.sub.4 is methyl and R.sub.2, R.sub.3 and R.sub.5 are each hydrogen.