Palladium-catalysed ortho-acylation of 6-anilinopurines/purine nucleosides via C-H activation

被引:16
作者
Allu, Srinivasarao [1 ]
Swamy, K. C. Kumara [1 ]
机构
[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Telangana, India
关键词
ALPHA-OXOCARBOXYLIC ACIDS; DECARBOXYLATIVE ORTHO-ACYLATION; OXIDATIVE ORTHO-ACYLATION; TERT-BUTYL HYDROPEROXIDE; TOLUENE DERIVATIVES; BOND ACTIVATION; DIRECTING GROUP; DIRECT ACCESS; 6-ARYLPURINE NUCLEOSIDES; AROMATIC-ALDEHYDES;
D O I
10.1039/c5ra18447a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Purinyl N1 directed ortho-acylation of 6-anilinopurines was achieved via C(sp(2))-H bond activation in the presence of [Pd]-catalyst using aldehydes or alpha-oxocarboxylic acids as the acylating source. A wide variety of purine appended 2'-aminoacetophenones/benzophenones are isolated in good to excellent yields. These catalytic transformations are also successfully applied to 6-anilinopurine nucleosides.
引用
收藏
页码:92045 / 92054
页数:10
相关论文
共 77 条
[1]   [RhCp*Cl2]2-Catalyzed Directed N-Boc Amidation of Arenes "on Water" [J].
Ali, Md Ashif ;
Yao, Xiayin ;
Sun, Hao ;
Lu, Hongjian .
ORGANIC LETTERS, 2015, 17 (06) :1513-1516
[2]   Ruthenium-Catalyzed Oxidative Annulation of 6-Anilinopurines with Alkynes via C-H Activation: Synthesis of Indole-Substituted Purines/Purine Nucleosides [J].
Allu, Srinivasarao ;
Swamy, K. C. Kumara .
ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (12) :2665-2680
[3]   Ruthenium-Catalyzed Synthesis of lsoquinolones with 8-Aminoquinoline as a Bidentate Directing Group in C-H Functionalization [J].
Allu, Srinivasarao ;
Swamy, K. C. Kumara .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (09) :3963-3972
[4]  
[Anonymous], 1997, SHELX 97 PROGRAM CRY
[5]   Palladium-catalysed regioselective aroylation and acetoxylation of 3,5-diarylisoxazole via ortho C-H functionalisations [J].
Banerjee, Arghya ;
Bera, Anupam ;
Santra, Sourav Kumar ;
Guin, Srimanta ;
Patel, Bhisma K. .
RSC ADVANCES, 2014, 4 (17) :8558-8566
[6]   Palladium-Catalyzed ortho-Aroylation of 2-Arylbenzothiazoles and 2-Arylbenzoxazoles with Aldehydes [J].
Banerjee, Arghya ;
Santra, Sourav Kumar ;
Guin, Srimanta ;
Rout, Saroj Kumar ;
Patel, Bhisma K. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (07) :1367-1376
[7]   Palladium-Catalyzed Oxidative sp2 C-H Bond Acylation with Aldehydes [J].
Basle, Olivier ;
Bidange, Johan ;
Shuai, Qi ;
Li, Chao-Jun .
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (07) :1145-1149
[8]   Benzyl bromides as aroyl surrogates in substrate directed Pd catalysed o-aroylation [J].
Behera, Ahalya ;
Ali, Wajid ;
Guin, Srimanta ;
Khatun, Nilufa ;
Mohanta, Prakash R. ;
Patel, Bhisma K. .
RSC ADVANCES, 2015, 5 (42) :33334-33338
[9]   Palladium-Catalyzed Regioselective C-H Acylation of Biaryl-2-amines [J].
Cai, Zhong-Jian ;
Yang, Chao ;
Wang, Shun-Yi ;
Ji, Shun-Jun .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (16) :7928-7936
[10]   Purinyl N1-Directed Aromatic C-H Oxidation in 6-Arylpurines and 6-Arylpurine Nucleosides [J].
Chamala, Raghu Ram ;
Parrish, Damon ;
Pradhan, Padmanava ;
Lakshman, Mahesh K. .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (15) :7423-7435