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
收藏
页码：6495 / 6499
页数：5
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