Synthesis of β- and γ-Carbolinones via Pd-Catalyzed Direct Dehydrogenative Annulation (DDA) of Indole-carboxamides with Alkynes Using Air as the Oxidant

被引：138
作者：
Shi, Zhuangzhi [1 ]
Cui, Yuxin [1 ]
Jiao, Ning [1 ,2 ]
机构：
[1] Peking Univ, State Key Lab Nat & Biomimet Drugs, Sch Pharmaceut Sci, Beijing 100083, Peoples R China
[2] E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China
来源：
ORGANIC LETTERS | 2010年 / 12卷 / 13期
基金：
美国国家科学基金会;
关键词：
C-H ACTIVATION; BOND FUNCTIONALIZATION; INTERNAL ALKYNES; OXIDATIVE CYCLIZATION; AROMATIC SUBSTITUTION; DERIVATIVES; PALLADIUM(II); ARYLATION; MULTIPLE; ANILINES;
D O I：
10.1021/ol1007839
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A palladium-catalyzed direct dehydrogenative annulation (DDA) of indolecarboxamides with internal alkynes via C-H and N-H bond cleavage using air as the oxidant was developed. With this method, both beta- and gamma-carbolinones can be easily prepared under the mild conditions.
引用
收藏
页码：2908 / 2911
页数：4
相关论文
共 53 条
[1]   Intramolecular Heck reaction of 2- and 3-iodoindole derivatives for the synthesis of β- and γ-carbolinones [J].
Beccalli, EM ;
Broggini, G ;
Marchesini, A ;
Rossi, E .
TETRAHEDRON, 2002, 58 (33) :6673-6678
[2]   Mild aerobic oxidative palladium (II) catalyzed C-H bond functionalization: Regioselective and switchable C-H alkenylation and annulation of pyrroles [J].
Beck, EM ;
Grimster, NP ;
Hatley, R ;
Gaunt, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (08) :2528-2529
[3]   Exclusive 5-exo-dig hydroarylation of o-alkynyl biaryls proceeding via C-H activation pathway [J].
Chernyak, Natalia ;
Gevorgyan, Vladimir .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (17) :5636-+
[4]  
CINCINELLI R, 2008, SYNTHESIS-STUTTGART, P1517
[5]   2-(QUINUCLIDIN-3-YL)PYRIDO[4,3-B]INDOL-1-ONES AND ISOQUINOLIN-1-ONES - POTENT CONFORMATIONALLY RESTRICTED 5-HT(3) RECEPTOR ANTAGONISTS [J].
CLARK, RD ;
MILLER, AB ;
BERGER, J ;
REPKE, DB ;
WEINHARDT, KK ;
KOWALCZYK, BA ;
EGLEN, RM ;
BONHAUS, DW ;
LEE, CH ;
MICHEL, AD ;
SMITH, WL ;
WONG, EHF .
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (18) :2645-2657
[6]   Pd(II)-Catalyzed Synthesis of Carbolines by Iminoannulation of Internal Alkynes via Direct C-H Bond Cleavage Using Dioxygen as Oxidant [J].
Ding, Shengtao ;
Shi, Zhuangzhi ;
Jiao, Ning .
ORGANIC LETTERS, 2010, 12 (07) :1540-1543
[7]   C-C bond formation via double C-H functionalization: Aerobic oxidative coupling as a method for synthesizing heterocoupled biaryls [J].
Dwight, Timothy A. ;
Rue, Nicholas R. ;
Charyk, Dagmara ;
Josselyn, Ryan ;
DeBoef, Brenton .
ORGANIC LETTERS, 2007, 9 (16) :3137-3139
[8]   Palladium-catalyzed intramolecular arylation reaction:: Mechanism and application for the synthesis of polyarenes [J].
Echavarren, AM ;
Gómez-Lor, B ;
González, JJ ;
de Frutos, O .
SYNLETT, 2003, (05) :585-597
[9]   Gold-catalyzed cycloisomerization of N-propargylindole-2-carboxamides:: Application toward the synthesis of lavendamycin analogues [J].
England, Dylan B. ;
Padwa, Albert .
ORGANIC LETTERS, 2008, 10 (16) :3631-3634
[10]   Lewis acid-directed cyclocondensation of piperidone enol ethers with 2-methoxy-4-(N-phenylsulfonyl)-1,4-benzoquinoneimine:: A new regioselective synthesis of oxygenated carbolines [J].
Engler, TA ;
Wanner, J .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (08) :2444-2457
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