Aniline → 3-Phenylquinazolinone

HRID 511778Notes

Reaction equation

HRID 511778 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[N:11]=[CH:10][NH:9][C:7](=O)[C:5]=2[CH:6]=1.[O:12]1C2C=CC=CC=2C=CN1.N[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[C:23]1([N:9]2[CH:7]=[C:5]3[C:4]([CH:3]=[CH:2][CH:1]=[CH:6]3)=[N:11][C:10]2=[O:12])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 6115AnilineHCID 17845026Benzoxazines2×HCID 1354087534(1H)-Quinazolinone

Product 1

HCID 671201143-Phenylquinazolinone

Procedure

The quinazolinone inhibitors (e.g., inhibitor compound formula D) of the general structure 16 (Scheme 4, below) are made in two steps from the commercially available benzoxazine 12 (Scheme 4). The benzoxazine is first heated with an aniline (13) to form 3-phenylquinazolinone derivative 14. This intermediate is then reacted with substituted furan-2-carboxaldehyde 15 in the presence of sodium acetate (NaOAc)/acetic acid (AcOH) to provide the desired quinazolinones 16.

Sources & evidence

ORD record
ord-1ac3f777fc0e40ab9fc99d1936f151c9
Source dataset
uspto-grants-2015_08
Patent number
US09101635B2

Reaction notes

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