Abstract
The reaction of methyl anthranilates with N-arylcyanamides in the presence of p-TsOH in t-BuOH under reflux afforded predominantly 3-arylquinazolin-4-ones. In contrast, the reaction of the same reactants with TMSCl in t-BuOH at 60 °C followed by the Dimroth rearrangement in aqueous ethanolic sodium hydroxide gave exclusively the regioisomers, 2-(N-arylamino)quinazolin-4-ones. The regioselective synthesis of N-aryl-substituted 2-aminoquinazolin-4-ones can be further applied to the synthesis of benzimidazo[2,1-b]quinazolin-12-ones.
| Original language | English |
|---|---|
| Pages (from-to) | 4482-4494 |
| Number of pages | 13 |
| Journal | Organic and Biomolecular Chemistry |
| Volume | 16 |
| Issue number | 24 |
| DOIs | |
| Publication status | Published - 2018 Jan 1 |
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ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
Cite this
Regioselective synthesis and biological evaluation of : N -substituted 2-aminoquinazolin-4-ones. / Liao, Zhen Yuan; Yeh, Wen Hsiung; Liao, Pen Yuan; Liu, Yu Ting; Chen, Ying Cheng; Chen, Yi Hung; Hsieh, Tsung Han; Lin, Chia Chi; Lu, Ming Hsuan; Chen, Yi Song; Hsu, Ming Chih; Li, Tsai Kun; Chien, Tun Cheng.
In: Organic and Biomolecular Chemistry, Vol. 16, No. 24, 01.01.2018, p. 4482-4494.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Regioselective synthesis and biological evaluation of
T2 - N -substituted 2-aminoquinazolin-4-ones
AU - Liao, Zhen Yuan
AU - Yeh, Wen Hsiung
AU - Liao, Pen Yuan
AU - Liu, Yu Ting
AU - Chen, Ying Cheng
AU - Chen, Yi Hung
AU - Hsieh, Tsung Han
AU - Lin, Chia Chi
AU - Lu, Ming Hsuan
AU - Chen, Yi Song
AU - Hsu, Ming Chih
AU - Li, Tsai Kun
AU - Chien, Tun Cheng
PY - 2018/1/1
Y1 - 2018/1/1
N2 - The reaction of methyl anthranilates with N-arylcyanamides in the presence of p-TsOH in t-BuOH under reflux afforded predominantly 3-arylquinazolin-4-ones. In contrast, the reaction of the same reactants with TMSCl in t-BuOH at 60 °C followed by the Dimroth rearrangement in aqueous ethanolic sodium hydroxide gave exclusively the regioisomers, 2-(N-arylamino)quinazolin-4-ones. The regioselective synthesis of N-aryl-substituted 2-aminoquinazolin-4-ones can be further applied to the synthesis of benzimidazo[2,1-b]quinazolin-12-ones.
AB - The reaction of methyl anthranilates with N-arylcyanamides in the presence of p-TsOH in t-BuOH under reflux afforded predominantly 3-arylquinazolin-4-ones. In contrast, the reaction of the same reactants with TMSCl in t-BuOH at 60 °C followed by the Dimroth rearrangement in aqueous ethanolic sodium hydroxide gave exclusively the regioisomers, 2-(N-arylamino)quinazolin-4-ones. The regioselective synthesis of N-aryl-substituted 2-aminoquinazolin-4-ones can be further applied to the synthesis of benzimidazo[2,1-b]quinazolin-12-ones.
UR - http://www.scopus.com/inward/record.url?scp=85049049779&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85049049779&partnerID=8YFLogxK
U2 - 10.1039/c8ob00624e
DO - 10.1039/c8ob00624e
M3 - Article
C2 - 29869668
AN - SCOPUS:85049049779
VL - 16
SP - 4482
EP - 4494
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
SN - 1477-0520
IS - 24
ER -