Silver-Catalyzed, Aldehyde-Induced α-C-H Functionalization of Tetrahydroisoquinolines with Concurrent C-P Bond Formation/N-Alkylation

被引:52
作者
Hu, Gaobo [1 ,2 ]
Chen, Weizhu [1 ,2 ,4 ]
Ma, Dumei [3 ]
Zhang, Yun [1 ,2 ]
Xu, Pengxiang [1 ,2 ]
Gao, Yuxing [1 ,2 ]
Zhao, Yufen [1 ,2 ]
机构
[1] Xiamen Univ, Coll Chem & Chem Engn, Dept Chem, Xiamen 361005, Fujian, Peoples R China
[2] Xiamen Univ, Coll Chem & Chem Engn, Key Lab Chem Biol Fujian Prov, Xiamen 361005, Fujian, Peoples R China
[3] Xiamen Univ, Coll Chem & Chem Engn, Dept Chem & Biochem Engn, Xiamen 361005, Fujian, Peoples R China
[4] State Ocean Adm, Inst Oceanog 3, Xiamen 361005, Fujian, Peoples R China
关键词
DEHYDROGENATIVE COUPLING REACTIONS; AMINOPHOSPHONIC ACIDS; BIOLOGICAL-ACTIVITY; SYNTHETIC METHODS; EFFICIENT; INHIBITORS; PHOSPHONATES; DERIVATIVES; CHEMISTRY; ANALOGS;
D O I
10.1021/acs.joc.5b02625
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first facile and efficient silver-catalyzed, aldehyde-induced three-component reaction of N-unprotected tetrahydroisoquinolines, aldehydes, and dialkyl phosphonates has been developed, providing a general one-step approach to structurally diverse C1-phosphonylated THIQs accompanied by concurrent C-P bond formation/N-alkylation with remarkable functional group tolerance and excellent regioselectivity for endo products.
引用
收藏
页码:1704 / 1711
页数:8
相关论文
共 52 条
[1]   CDC Reactions of N-Aryl Tetrahydroisoquinolines Using Catalytic Amounts of DDQ: C-H Activation under Aerobic Conditions [J].
Alagiri, Kaliyamoorthy ;
Devadig, Pradeep ;
Prabhu, Kandikere R. .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (17) :5160-5164
[2]   Molybdenum trioxide catalyzed oxidative cross-dehydrogenative coupling of benzylic sp3 C-H bonds: synthesis of α-aminophosphonates under aerobic conditions [J].
Alagiri, Kaliyamoorthy ;
Devadig, Pradeep ;
Prabhu, Kandikere R. .
TETRAHEDRON LETTERS, 2012, 53 (12) :1456-1459
[3]   Synthesis of new α aminophosphonate system bearing Indazole moiety and their biological activity [J].
Ali, Nasir Ali Shafakat ;
Zakir, Shaikh ;
Patel, Muqtadir ;
Farooqui, Mazahar .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 50 :39-43
[4]   Synthetic methods of cyclic α-aminophosphonic acids and their esters [J].
Ali, Tarik E. .
ARKIVOC, 2014, :21-91
[5]   RENIN INHIBITORS - SYNTHESIS OF TRANSITION-STATE ANALOG INHIBITORS CONTAINING PHOSPHORUS-ACID DERIVATIVES AT THE SCISSILE BOND [J].
ALLEN, MC ;
FUHRER, W ;
TUCK, B ;
WADE, R ;
WOOD, JM .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (07) :1652-1661
[6]   Silver-mediated synthesis of heterocycles [J].
Alvarez-Corral, Miriam ;
Munoz-Dorado, Manuel ;
Rodirguez-Garcia, Ignacio .
CHEMICAL REVIEWS, 2008, 108 (08) :3174-3198
[7]   Copper-catalyzed aerobic phosphonation of sp3 C-H bonds [J].
Basle, Olivier ;
Li, Chao-Jun .
CHEMICAL COMMUNICATIONS, 2009, (27) :4124-4126
[8]   Zirconium(IV) compounds as efficient catalysts for synthesis of α-aminophosphonates [J].
Bhagat, Srikant ;
Chakraborti, Asit K. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (15) :6029-6032
[9]   The development of first Staphylococcus aureus SplB protease inhibitors: Phosphonic analogues of glutamine [J].
Burchacka, Ewa ;
Walczak, Maciej ;
Sienczyk, Marcin ;
Dubin, Grzegorz ;
Zdzalik, Michal ;
Potempa, Jan ;
Oleksyszyn, Jozef .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (17) :5574-5578
[10]   Synthesis and Antiviral Activities of Chiral Thiourea Derivatives Containing an α-Aminophosphonate Moiety [J].
Chen, Mei-Hang ;
Chen, Zhuo ;
Song, Bao-An ;
Bhadury, Pinaki S. ;
Yang, Song ;
Cai, Xue-Jian ;
Hu, De-Yu ;
Xue, Wei ;
Zeng, Song .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2009, 57 (04) :1383-1388