Transition-Metal-Free Arylation of N-Alkyl-tetrahydroisoquinolines under Oxidative Conditions: A Convenient Synthesis of C1-Arylated Tetrahydroisoquinoline Alkaloids

被引:27
作者
Singh, Kamal Nain [1 ,2 ]
Kessar, Satinder V. [1 ,2 ]
Singh, Paramjit [1 ,2 ]
Singh, Pushpinder [3 ]
Kaur, Manjot [1 ,2 ]
Batra, Aanchal [1 ,2 ]
机构
[1] Panjab Univ, Dept Chem, Chandigarh 160014, India
[2] Panjab Univ, Ctr Adv Studies Chem, Chandigarh 160014, India
[3] DAV Univ, Dept Chem, Jalandhar 144025, India
来源
SYNTHESIS-STUTTGART | 2014年 / 46卷 / 19期
关键词
arylation; tetrahydroisoquinoline; C-H activation; alkaloids; metal-free; SP(3) C-H; DEHYDROGENATIVE COUPLING REACTIONS; ONE-POT SYNTHESIS; TERTIARY-AMINES; HIGHLY EFFICIENT; BOND ARYLATION; 1-ARYL-TETRAHYDROISOQUINOLINE ANALOGS; DIRECT FUNCTIONALIZATION; NUCLEOPHILIC-ADDITION; CRYPTOSTYLINE-II;
D O I
10.1055/s-0034-1378337
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple protocol for the C1 arylation of tetrahydroisoquinolines with aryl Grignard reagents via diethyl azodicarboxylate (DEAD) mediated oxidative C-H activation under metal-free conditions has been developed. The target compounds, including some naturally occurring alkaloids, were obtained in moderate to good yields.
引用
收藏
页码:2644 / 2650
页数:7
相关论文
共 95 条
[71]   Cross-Dehydrogenative Coupling of Dithiolanes with Ketones and Indoles under Metal-Free Conditions [J].
Singh, Kamal Nain ;
Singh, Paramjit ;
Singh, Pushpinder ;
Maheshwary, Yogita ;
Kessar, Satinder V. ;
Batra, Aanchal .
SYNLETT, 2013, 24 (15) :1963-1967
[72]   C-1 Alkynylation of N-Methyltetrahydroisoquinolines through CDC: A Direct Access to Phenethylisoquinoline Alkaloids [J].
Singh, Kamal Nain ;
Singh, Paramjit ;
Kaur, Amarjit ;
Singh, Pushpinder .
SYNLETT, 2012, (05) :760-764
[73]   Nucleophilic Addition of β-Amino Carbanions to Arynes: One-Pot Synthesis of 4-Aryl-N-methyl-1,2,3,4-tetrahydroisoquinolines [J].
Singh, Kemal Nain ;
Singh, Paramjit ;
Singh, Pushpinder ;
Deol, Yadwinder Singh .
ORGANIC LETTERS, 2012, 14 (09) :2202-2205
[74]   Oxidative C-Se Coupling of Formamides and Diselenides by Using Aqueous tert-Butyl Hydroperoxide: A Convenient Synthesis of Selenocarbamates [J].
Singh, Pushpinder ;
Batra, Aanchal ;
Singh, Paramjit ;
Kaur, Amarjit ;
Singh, Kamal Nain .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (34) :7688-7692
[75]   A Concise Synthesis of Tetrabenazine: An Intramolecular Aza-Prins-Type Cyclization via Oxidative C-H Activation [J].
Son, Young Wook ;
Kwon, Tae Hui ;
Lee, Jae Kyun ;
Rae, Ae Nim ;
Lee, Jae Yeol ;
Cho, Yong Seo ;
Min, Sun-Joon .
ORGANIC LETTERS, 2011, 13 (24) :6500-6503
[76]   Solvent-Free Cross-Dehydrogenative Coupling Reactions under High Speed Ball-Milling Conditions Applied to the Synthesis of Functionalized Tetrahydroisoquinolines [J].
Su, Weike ;
Yu, Jingbo ;
Li, Zhenhua ;
Jiang, Zhijiang .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (21) :9144-9150
[77]  
SUZUKI H, 1995, TETRAHEDRON LETT, V36, P6709, DOI 10.1016/00404-0399(50)1358O-
[78]   SYNTHESIS OF RACEMIC CRYPTOSTYLINE-I, CRYPTOSTYLINE-II, CRYPTOSTYLINE-III BY RADICAL CYCLIZATION [J].
TAKANO, S ;
SUZUKI, M ;
KIJIMA, A ;
OGASAWARA, K .
CHEMISTRY LETTERS, 1990, (02) :315-316
[79]   Highly enantioselective catalytic acyl-Pictet-Spengler reactions [J].
Taylor, MS ;
Jacobsen, EN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (34) :10558-10559
[80]   Synthesis, antibacterial activity and QSAR studies of 1,2-disubstituted-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolines [J].
Tiwari, RK ;
Singh, D ;
Singh, J ;
Chhillar, AK ;
Chandra, R ;
Verma, AK .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2006, 41 (01) :40-49