Enantioselective Michael addition using 4(3H)-pyrimidinone

被引：0

作者：

Chen, Yong-Sin ^{[1
]}

Huang, Ming-Hsuan ^{[1
]}

Cheng, Yan-Peng ^{[1
]}

Hou, Duen-Ren ^{[1
]}

机构：

[1] Natl Cent Univ, Dept Chem, 300 Jhong Da Rd, Taoyuan 32001, Taiwan

来源：

JOURNAL OF THE CHINESE CHEMICAL SOCIETY | 2022年 / 69卷 / 08期

关键词：

4-pyrimidinone; enantioselective; Michael addition; organocatalysis; ONE-POT SYNTHESIS; PYRIMIDINONE DERIVATIVES; CONFORMATIONAL-ANALYSIS; FEBRIFUGINE; INHIBITORS; DISCOVERY; ANALOGS; ACID;

D O I：

10.1002/jccs.202200105

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The framework of 4-pyrimidinones is prevalent in biologically and medicinally important molecules. Here we report that chiral N-substituted 4-pyrimidinones were prepared by an enantioselective, organocatalytic aza-Michael addition of 4(3H)-pyrimidinone (4-hydroxypyrimidine) to alpha,beta-unsaturated 1,4-dicarbonyl compounds for the first time. The reactions were optimized by the choice of solvents, screening Cinchona alkaloid-based bifunctional catalysts, and Michael acceptors to achieve good yields and enantioselectivities.

引用

页码：1462 / 1474

页数：13

共 50 条

[1] EXPLOSION IN PREPARATION OF 5-BROMO-4(3H)-PYRIMIDINONE
DIETSCHE, TJ
POWERS, B
CHEMICAL & ENGINEERING NEWS, 1995, 73 (28) : 4 - 4
[2] ADDITION OF MICHAEL DES INDOL-2(3H)-ONES
GRUDA, I
TETRAHEDRON LETTERS, 1973, (06) : 457 - 460
[3] Diaminomethyleneaminocarbonyldinitromethane, formed during the preparation of 2-amino-6-chloro-5-nitro-4(3H)-pyrimidinone by nitration of 2-amino-6-chloro-4(3H)-pyrimidinone
Boyle, PH
Daly, KM
Leurquin, F
Robinson, JK
Scully, DT
TETRAHEDRON LETTERS, 2001, 42 (09) : 1793 - 1795
[4] HETEROCYCLIZATION OF 5-ETHYL-2-METHALLYLTHIO-6-METHYL-4(3H)-PYRIMIDINONE USING ACIDS
Frolova, T. V.
Slepuhin, P. A.
Kim, D. G.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2011, 47 (02) : 252 - 254
[5] 6-ALKYL-2-METHOXY-4(3H)-PYRIMIDINONE AND 5,6-DIALKYL-2-METHOXY-4(3H)-PYRIMIDINONE IN THE TRANSFORMATIONS OF PYRIMIDINES - REGIOSPECIFIC 1-N-ACYLATION OF PYRIMIDINES
BOTTA, M
DEANGELIS, F
FINIZIA, G
NICOLETTI, R
DELFINI, M
TETRAHEDRON LETTERS, 1985, 26 (28) : 3345 - 3348
[6] Chiral Amine Thiourea-Promoted Enantioselective Michael Addition Reactions of 3-Substituted Benzofuran-2(3H)-ones to Maleimides
Li, Xin
Hu, Shenshen
Xi, Zhiguo
Zhang, Long
Luo, Sanzhong
Cheng, Jin-Pei
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (24): : 8697 - 8700
[7] Heterocyclization of 5-ethyl- 2-methallylthio-6-methyl-4(3H)-pyrimidinone using acids
T. V. Frolova
P. A. Slepuhin
D. G. Kim
Chemistry of Heterocyclic Compounds, 2011, 47 : 252 - 254
[8] Highly diastereo-and enantioselective Michael addition of 3-substituted benzofuran-2(3H)-ones to 4-oxo-enoates catalyzed by lanthanide(III) complexes
Wang, Zhen
Yao, Qian
Kang, Tengfei
Feng, Juhua
Liu, Xiaohua
Lin, Lili
Feng, Xiaoming
CHEMICAL COMMUNICATIONS, 2014, 50 (38) : 4918 - 4920
[9] Synthesis of new derivatives of 6-(1-adamantylmethyl)-4(3H)-pyrimidinone
Novakov, I. A.
Orlinson, B. S.
Navrotskii, M. B.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 45 (02) : 316 - 317
[10] Synthesis of new derivatives of 6-(1-adamantylmethyl)-4(3H)-pyrimidinone
I. A. Novakov
B. S. Orlinson
M. B. Navrotskii
Russian Journal of Organic Chemistry, 2009, 45 : 316 - 317

← 1 2 3 4 5 →