Enantioselective synthesis of dihydroquinazolinone derivatives catalyzed by a chiral organocatalyst

被引：15

作者：

Ayyanar, Siva ^{[1
]}

Vijaya, Ponmuthu Kottala ^{[1
]}

Mariyappan, Madhappan ^{[1
]}

Ashokkumar, Veeramanoharan ^{[1
]}

Sadhasivam, Velu ^{[1
]}

Balakrishnan, Sankar ^{[1
]}

Chinnadurai, Chithiraikumar ^{[1
]}

Murugesan, Sepperumal ^{[1
]}

机构：

[1] Madurai Kamaraj Univ, Sch Chem, Dept Inorgan Chem, Supramol & Organometall Chem Lab, Madurai 625021, Tamil Nadu, India

来源：

NEW JOURNAL OF CHEMISTRY | 2017年 / 41卷 / 16期

关键词：

HIGHLY EFFICIENT SYNTHESIS; ASYMMETRIC-SYNTHESIS; INTRAMOLECULAR AMIDATION; 2,3-DIHYDROQUINAZOLIN-4(1H)-ONES; IMINES; WATER; ACID; QUINAZOLIN-4(3H)-ONES; TRIFLATE; AGENTS;

D O I：

10.1039/c7nj00538e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The asymmetric condensation/amine addition cascade sequence of 2-aminobenzamide and aldehydes, catalyzed by a novel chiral organocatalyst, was realized. The organocatalyst was found to be very effective and highly enantioselective for such cascade reactions at room temperature, affording 2,3-dihydroquinazolinones in excellent yields (up to 99%) with enantiomeric excesses of up to 97%. The best level of stereocontrol was obtained for aromatic/aliphatic aldehydes with ortho, para or meta substituents.

引用

页码：7980 / 7986

页数：7

共 30 条

[1] ANTIBACTERIAL 2,3-DIHYDRO-2-(5-NITRO-2-THIENYL)-QUINAZOLIN-4(1H)-ONES
ALAIMO, RJ
RUSSELL, E
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1972, 15 (03) : 335 - &
[2] Synthesis of 3-(aryl)-2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives using heteropolyacids as green, heterogeneous and recyclable catalysts
Allameh, S.
Heravi, M. M.
Hashemi, M. M.
Bamoharram, F. F.
[J]. CHINESE CHEMICAL LETTERS, 2011, 22 (02) : 131 - 134
[3] 1-AMINOACYL-2,3-DIHYDRO-4(1H)-QUINAZOLINONE DERIVATIVES WITH CHOLERETIC AND ANTIFIBRILLATORY ACTIVITY
BONOLA, G
DARE, P
MAGISTRE.MJ
MASSARAN.E
SETNIKAR, I
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1968, 11 (06) : 1136 - &
[4] A facile synthesis of 2,3-dihydro-2-aryl-4(1H)-quinazolinones catalyzed by scandium(III) triflate
Chen, Jiu Xi
Wu, Hua Yue
Su, Wei Ke
[J]. CHINESE CHEMICAL LETTERS, 2007, 18 (05) : 536 - 538
[5] Gallium(III) triflate-catalyzed one-pot selective synthesis of 2 3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones
Chen, Jiuxi
Wu, Dengze
He, Fei
Liu, Miaochang
Wu, Huayue
Ding, Jinchang
Su, Weike
[J]. TETRAHEDRON LETTERS, 2008, 49 (23) : 3814 - 3818
[6] Eco-friendly synthesis of 2,3-dihydroquinazolin-4(1H)-ones in ionic liquids or ionic liquid-water without additional catalyst
Chen, Jiuxi
Su, Weike
Wu, Huayue
Liu, Miaochang
Jin, Can
[J]. GREEN CHEMISTRY, 2007, 9 (09) : 972 - 975
[7] Catalytic Asymmetric Synthesis of Dihydroquinazolinones from Imines and 2-Aminobenzamides
Cheng, Dao-Juan
Tian, Yu
Tian, Shi-Kai
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (06) : 995 - 999
[8] Direct Catalytic Asymmetric Synthesis of Cyclic Aminals from Aldehydes
Cheng, Xu
Vellalath, Sreekumar
Goddard, Richard
List, Benjamin
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (47) : 15786 - +
[9] Asymmetric synthesis of 2,3-dihydro-2-arylquinazolin-4-ones: Methodology and application to a potent fluorescent tubulin inhibitor with anticancer activity
Chinigo, Gary M.
Paige, Mikell
Grindrod, Scott
Hamel, Ernest
Dakshanamurthy, Sivanesan
Chruszcz, Maksymilian
Minor, Wladek
Brown, Milton L.
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (15) : 4620 - 4631
[10] Highly enantioselective synthesis of dihydroquinazolinones through Sc(OTf)3-catalyzed intramolecular amidation of imines
Deng, Tao
Wang, Hongjun
Cai, Chun
[J]. JOURNAL OF FLUORINE CHEMISTRY, 2015, 169 : 72 - 77

← 1 2 3 →