Synthesis of diversely substituted quinazoline-2,4(1H,3H)-diones by cyclization of tert-butyl (2-cyanoaryl)carbamates

被引：0

作者：

Kovela, Satish ^{[1
]}

Karad, Somnath ^{[1
]}

Tatipudi, V. V. Ganesh ^{[1
]}

Arumugam, Karthikeyan ^{[1
]}

Somwanshi, Atul Vijay ^{[1
]}

Muthukumar, M. ^{[1
]}

Mathur, Arvind ^{[2
]}

Tester, Richland ^{[2
]}

机构：

[1] Biocon Bristol Myers Squibb Res Ctr, Dept Discovery Synth, Bengaluru 560099, Karnataka, India

[2] Bristol Myers Squibb, Dept Discovery Synth, POB 4000, Princeton, NJ 08540 USA

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2024年 / 22卷 / 32期

关键词：

CARBON-DIOXIDE; CHEMICAL FIXATION; IONIC LIQUIDS; DERIVATIVES; CO2; INHIBITORS; QUINAZOLINES; EFFICIENT; QUINAZOLINE-2,4-DIONES; 2-AMINOBENZONITRILE;

D O I：

10.1039/d4ob00885e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of diversely substituted quinazoline-2,4(1H,3H)-diones by cyclization of tert-butyl (2-cyanoaryl)carbamates using readily accessible Boc protected o-amino nitriles is reported. The reaction proceeds smoothly at room temperature using 1 equiv. of H2O2 under basic conditions. This reaction is compatible with a variety of aromatic/heteroaromatic substrates with different functional groups. This strategy can be utilized for the simplified synthesis of goshuyuamide II and an alkaloid isolated from Zanthoxylum arborescens in good yields. This method was also applied to the synthesis of quinazoline-2,4(1H,3H)-diones that are precursors of medicinally important compounds: alfuzosin, terazosin, prazosin, IAAP, doxazosin, FK 366 (zenarestat) and KF31327.

引用

页码：6495 / 6499

页数：5

共 50 条

[41] Synthesis of Quinazoline-2,4(1H,3H)-Diones from Carbon dioxide and 2-Aminobenzonitriles Using MgO/ZrO2 as a Solid Base Catalyst [J].

Patil, Yogesh P. ;

Tambade, Pawan J. ;

Parghi, Kalpesh D. ;

Jayaram, Radha V. ;

Bhanage, Bhalchandra M. .

CATALYSIS LETTERS, 2009, 133 (1-2) :201-208

[42] Efficient One Pot Capture and Conversion of CO2 into Quinazoline-2,4(1H,3H)-diones Using Triazolium-Based Ionic Liquids [J].

Liu, Fusheng ;

Ping, Ran ;

Gu, Yongqiang ;

Zhao, Penghui ;

Liu, Bin ;

Gao, Jun ;

Liu, Mengshuai .

ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2020, 8 (07) :2910-2918

[43] Synthesis of Quinazoline-2,4(1H,3H)-Diones from Carbon dioxide and 2-Aminobenzonitriles Using MgO/ZrO2 as a Solid Base Catalyst [J].

Yogesh P. Patil ;

Pawan J. Tambade ;

Kalpesh D. Parghi ;

Radha V. Jayaram ;

Bhalchandra M. Bhanage .

Catalysis Letters, 2009, 133 :201-208

[44] Efficient [WO4]2--Catalyzed Chemical Fixation of Carbon Dioxide with 2-Aminobenzonitriles to Quinazoline-2,4(1H,3H)-diones [J].

Kimura, Toshihiro ;

Sunaba, Hanako ;

Kamata, Keigo ;

Mizuno, Noritaka .

INORGANIC CHEMISTRY, 2012, 51 (23) :13001-13008

[45] A theoretical study on the efficiency and role of guanidines-based organic superbases on carbon dioxide utilization in quinazoline-2,4(1H, 3H)-diones synthesis [J].

Hossein Sabet-Sarvestani ;

Hossein Eshghi ;

Mohammad Izadyar .

Structural Chemistry, 2017, 28 :675-686

[46] Biocompatible anions-derived ionic liquids a sustainable media for CO2 conversion into quinazoline-2,4(1H,3H)-diones under additive-free conditions [J].

Weng, Shiwei ;

Dong, Jiqing ;

Ma, Jingjing ;

Bai, Jiayu ;

Liu, Fusheng ;

Liu, Mengshuai .

JOURNAL OF CO2 UTILIZATION, 2022, 56

[47] Synthesis of N-Unsubstituted and N3-Substituted Quinazoline-2,4(1H,3H)-diones from o-Aminobenzamides and CO2 at Atmospheric Pressure and Room Temperature [J].

Zhang, Lin ;

Chen, Qian ;

Li, Linlin ;

Ma, Nana ;

Tian, Jie ;

Sun, Hao ;

Xu, Qian ;

Yang, Yuanyong ;

Li, Chun .

ORGANIC LETTERS, 2023, 25 (14) :2471-2475

[48] Green Synthesis of Dy2Sn2O7 Nanostructures Employing Gum of Ferula Assa Feotida for Formation of N3-substituted Quinazoline-2,4(1H,3H)-diones [J].

Sharafkhani, Javad ;

Zhiani, Rahele ;

Motavalizadehkakhky, Alireza ;

Mehrzad, Jamshid ;

Sadeghzadeh, Seyed Mohsen .

LETTERS IN ORGANIC CHEMISTRY, 2024, 21 (03) :229-237

[49] New acetamide derivatives of quinazoline-2,4(1H,3H)-dione: neural network prediction, synthesis, and psychotropic activity [J].

Perfilev, M. A. ;

Vassiliev, P. M. ;

Ozerov, A. A. ;

Maltsev, D. V. ;

Pluzhnikova, A. R. ;

Merezhkina, D. V. .

RUSSIAN CHEMICAL BULLETIN, 2023, 72 (04) :1075-1082

[50] New acetamide derivatives of quinazoline-2,4(1H,3H)-dione: neural network prediction, synthesis, and psychotropic activity [J].

M. A. Perfilev ;

P. M. Vassiliev ;

A. A. Ozerov ;

D. V. Maltsev ;

A. R. Pluzhnikova ;

D. V. Merezhkina .

Russian Chemical Bulletin, 2023, 72 :1075-1082

← 1 2 3 4 5 →