Mild and efficient TBAI-catalyzed synthesis of 1,2,3-benzotriazine-4-(3H)-ones from tert-butyl nitrite and 2-aminobenzamides under acid-free conditions

被引:23
作者
Yan, Yizhe [1 ,2 ]
Li, Hongyi [1 ]
Niu, Bin [1 ]
Zhu, Changrui [1 ]
Chen, Ting [1 ]
Liu, Yanqi [1 ]
机构
[1] Zhengzhou Univ Light Ind, Sch Food & Biol Engn, Zhengzhou 450000, Peoples R China
[2] Collaborat Innovat Ctr Food Prod & Safety, Zhengzhou, Henan Province, Peoples R China
关键词
1,2,3-Benzotriazine-4-(3H)-ones; tert-Butyl nitrite; 2-Aminobenzamides; Tetrabutylammonium iodide; Acid-free; TEMPO; (BUONO)-BU-T; DERIVATIVES; NITRATION; ALKYNES; ACCESS;
D O I
10.1016/j.tetlet.2016.07.102
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile and efficient annulation of 2-aminobenzamides and tert-butyl nitrite was developed, affording 1,2,3-benzotriazine-4-(3H)-ones in good yields under mild conditions. Notably, the reaction was carried out in the absence of strong acid and tert-butyl nitrite was employed as the nitrogen source. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4170 / 4173
页数:4
相关论文
共 23 条
[1]   1,2,3-BENZOTRIAZIN-4(3H)-ONES AND RELATED SYSTEMS .5. THERMOLYSIS OF 3-ARYL-1,2,3-BENZOTRIAZIN-4(3H)-ONES AND 3-ALKENYL-1,2,3-BENZOTRIAZIN-4(3H)-ONES [J].
BARKER, AJ ;
PATERSON, TM ;
SMALLEY, RK ;
SUSCHITZKY, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (09) :2203-2208
[2]   Preparation and local anaesthetic activity of benzotriazinone and benzoyltriazole derivatives [J].
Caliendo, G ;
Fiorino, F ;
Grieco, P ;
Perissutti, E ;
Santagada, V ;
Meli, R ;
Raso, GM ;
Zanesco, A ;
De Nucci, G .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1999, 34 (12) :1043-1051
[3]   Dehydrogenative N-Incorporation: A Direct Approach to Quinoxaline N-Oxides under Mild Conditions [J].
Chen, Feng ;
Huang, Xiaoqiang ;
Li, Xinyao ;
Shen, Tao ;
Zou, Miancheng ;
Jiao, Ning .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (39) :10495-10499
[4]   ANTITUMOR IMIDAZOTETRAZINES .32. SYNTHESIS OF NOVEL IMIDAZOTETRAZINONES AND RELATED BICYCLIC HETEROCYCLES TO PROBE THE MODE OF ACTION OF THE ANTITUMOR DRUG TEMOZOLOMIDE [J].
CLARK, AS ;
DEANS, B ;
STEVENS, MFG ;
TISDALE, MJ ;
WHEELHOUSE, RT ;
DENNY, BJ ;
HARTLEY, JA .
JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (09) :1493-1504
[5]   Metal-free nitrative cyclization of N-aryl imines with tert-butyl nitrite: dehydrogenative access to 3-nitroindoles [J].
Deng, Guo-Bo ;
Zhang, Jia-Ling ;
Liu, Yan-Yun ;
Liu, Bang ;
Yang, Xu-Heng ;
Li, Jin-Heng .
CHEMICAL COMMUNICATIONS, 2015, 51 (10) :1886-1888
[6]   Aerobic Oxynitration of Alkynes with tBuONO and TEMPO [J].
Dutta, Uttarn ;
Maity, Soham ;
Kancherla, Rajesh ;
Maiti, Debabrata .
ORGANIC LETTERS, 2014, 16 (24) :6302-6305
[7]   Asymmetric Synthesis of Axially Chiral Isoquinolones: Nickel-Catalyzed Denitrogenative Transannulation [J].
Fang, Zhi-Jia ;
Zheng, Sheng-Cai ;
Guo, Zhen ;
Guo, Jing-Yao ;
Tan, Bin ;
Liu, Xin-Yuan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (33) :9528-9532
[8]   1,2,3-BENZOTRIAZINE SULFONAMIDES - NEW CLASS OF ORAL DIURETIC AGENTS [J].
GADEKAR, SM ;
FREDERICK, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (04) :1383-+
[9]   SOME HALOGENATED 1,2,3-BENZOTRIAZIN-4(3H)ONES [J].
GADEKAR, SM ;
ROSS, E .
JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (02) :613-&
[10]   Facile Synthesis of Disubstituted Isoxazoles from Homopropargylic Alcohol via C=N Bond Formation [J].
Gao, Pin ;
Li, Hong-Xia ;
Hao, Xin-Hua ;
Jin, Dong-Po ;
Chen, Dao-Qian ;
Yan, Xiao-Biao ;
Wu, Xin-Xing ;
Song, Xian-Rong ;
Liu, Xue-Yuan ;
Liang, Yong-Min .
ORGANIC LETTERS, 2014, 16 (24) :6298-6301