Palladium Catalyzed Cross-Dehydrogenative Coupling/Annulation Reaction: A Practical and Efficient Approach to Hydroxyisoindolo[1,2-b]quinazolinone

被引:19
作者
Dabiri, Minoo [1 ]
Lehi, Noushin Farajinia [1 ]
Movahed, Siyavash Kazemi [1 ]
Khavasi, Hamid Reza [1 ]
机构
[1] Shahid Beheshti Univ, Fac Chem & Petr Sci, Dist 1,Daneshjou Blvd, Tehran 1983969411, Tehran Province, Iran
关键词
C-H activation; Palladium; Acylation; Annulation; Aldehydes; C-H; NATURAL-PRODUCTS; ACYLATION; QUINAZOLINONES; ALDEHYDES; QUINAZOLIN-4(3H)-ONES; ANILIDES; BONDS;
D O I
10.1002/ejoc.201900417
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The palladium-catalyzed cross-dehydrogenative coupling (CDC) followed by an intramolecular cyclization between arylquinazolinones and aldehydes has been described. This viable transformation provides a variety of novel substituted hydroxyisoindolo[1,2-b]quinazolinone compounds in moderate to good yields. Additionally, the reaction is performed with toluene in place of benzaldehyde by using an excess amount of tert-butyl hydroperoxide (TBHP) as the oxidant in good yield.
引用
收藏
页码:2933 / 2940
页数:8
相关论文
共 38 条
[11]   Palladium-catalyzed benzo[d]isoxazole synthesis by C-H activation/[4+1] annulation [J].
Duan, Pingping ;
Yang, Yunfang ;
Ben, Rong ;
Yan, Yiyong ;
Dai, Lu ;
Hong, Mei ;
Wu, Yun-Dong ;
Wang, Dongqi ;
Zhang, Xinhao ;
Zhao, Jing .
CHEMICAL SCIENCE, 2014, 5 (04) :1574-1578
[12]   Total Synthesis of a Pyrroloindoloquinazoline Alkaloid [J].
Gahtory, Digvijay ;
Chouhan, Mangilal ;
Sharma, Ratnesh ;
Nair, Vipin A. .
ORGANIC LETTERS, 2013, 15 (15) :3942-3945
[13]  
Girard S. A., 2013, ANGEW CHEM, V125, P76
[14]   The Cross-Dehydrogenative Coupling of Csp3-H Bonds: A Versatile Strategy for C-C Bond Formations [J].
Girard, Simon A. ;
Knauber, Thomas ;
Li, Chao-Jun .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (01) :74-100
[15]   Recent synthetic and medicinal perspectives of tryptanthrin [J].
Kaur, Ramandeep ;
Manjal, Sundeep Kaur ;
Rawal, Ravindra K. ;
Kumar, Kapil .
BIOORGANIC & MEDICINAL CHEMISTRY, 2017, 25 (17) :4533-4552
[16]   Synthesis of quinazolinones from anthranilamides and aldehydes via metal-free aerobic oxidation in DMSO [J].
Kim, Na Yeun ;
Cheon, Cheol-Hong .
TETRAHEDRON LETTERS, 2014, 55 (15) :2340-2344
[17]   Recent developments in the chemistry of quinazolinone alkaloids [J].
Kshirsagar, U. A. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (36) :9336-9352
[18]   Transition-Metal-Catalyzed C-H Functionalization for Construction of Quaternary Carbon Centers [J].
Li, Yang ;
Xu, Silong .
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (61) :16218-16245
[19]   Rhodium(III)-Catalyzed Indazole Synthesis by C-H Bond Functionalization and Cyclative Capture [J].
Lian, Yajing ;
Bergman, Robert G. ;
Lavis, Luke D. ;
Ellman, Jonathan A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (19) :7122-7125
[20]   Tryptanthrin Inhibits Angiogenesis by Targeting the VEGFR2-Mediated ERK1/2 Signalling Pathway [J].
Liao, Xuemei ;
Zhou, Xuelin ;
Mak, Nai-ki ;
Leung, Kwok-nam .
PLOS ONE, 2013, 8 (12)