Base dependent purported synthesis of congested 2-aminobenzylamines and tetrahydro-2-oxoquinazolines from 2-pyranones

被引：3
|
作者：
Farhanullah [1 ]
Samrin, Farhana [2 ]
Ram, Vishnu Ji [2 ]
机构：
[1] Natl Univ Singapore, Fac Sci, Dept Chem, Singapore 117543, Singapore
[2] Inst Engn & Technol, Dept Appl Chem, Lucknow, Uttar Pradesh, India
来源：
TETRAHEDRON | 2009年 / 65卷 / 08期
关键词：
POTENTIAL ANTIHYPERTENSIVE AGENTS; S; S-DIALKYL DITHIOCARBONATES; OXIDATIVE CARBONYLATION; UREAS; INHIBITORS; SYSTEMS; DERIVATIVES; DESIGN; AMINES;
D O I：
10.1016/j.tet.2008.12.041
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An expeditious and concise synthesis of highly congested 2-amino-3-aminomethyl-5-methylsulfanyl/-sec-aminobiphenyl-4-carbonitrile 4 and 1-tert-butoxycarbonyl-6-sec-amino-8-aryl-5-cyano-2-oxo-1,2,3, 4-tetrahydroquinazoline 5 has been delineated through base catalyzed ring transformation of 6-aryl-4-methylsulfanyl/-sec-amino-2H-pyran-2-one-3-carbonitrile 1 with 1,3-bis(tert-butoxycarbonylamino)-2-propanone 2, followed by TFA catalyzed hydrolysis of the intermediate [3-tert-butoxycarbonyl-aminomethyl-4-cyano-5-methylsulfanyl/-sec-aminobiphenyl-2-yl]carbamic acid tert-butyl ester 3 in moderate yield. The mechanism of formation of 5 has been established through isolation and transformation of the intermediate 3 to the 1-tert-butoxycarbonyl-6-sec-amino-8-aryl-5-cyano-2-oxo-1,2,3,4-tetrahydroquinazoline. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1635 / 1638
页数：4
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