Synthesis of novel azole-fused quinazolines via one-pot, sequential Ullmann-type coupling and intramolecular dehydrogenative C-N bonding

被引：33

作者：

Nandwana, Nitesh Kumar ^{[1
]}

Pericherla, Kasiviswanadharaju ^{[1
]}

Kaswan, Pinku ^{[1
]}

Kumar, Anil ^{[1
]}

机构：

[1] Birla Inst Technol & Sci, Dept Chem, Pilani 333031, Rajasthan, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 10期

关键词：

H FUNCTIONALIZATION; DIRECT ARYLATION; COPPER; AMINATION; AGENTS;

D O I：

10.1039/c4ob02375g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient one-pot sequential procedure is described for the synthesis of novel azole-fused quinazolines through Pd/Cu co-catalyzed, Ullmann-type coupling followed by cross dehydrogenative coupling of various azoles such as 1H-imidazole, 1H-benzimidazole and 1H-1,2,4-triazole with 2-(2-bromophenyl)1H-imidazole/benzimidazoles. The developed strategy has offered good yields (52-81%) of diverse N-fused tetra-, penta- and hexa-cyclic frameworks in a single step.

引用

页码：2947 / 2950

页数：4

共 30 条

[21]

Park T. Y., 2010, Korean patent, Patent No. 2010097797

[22] Copper-Catalyzed Tandem Azide-Alkyne Cycloaddition, Ullmann Type C-N Coupling, and Intramolecular Direct Arylation [J].

Pericherla, Kasiviswanadharaju ;

Jha, Amitabh ;

Khungar, Bharti ;

Kumar, Anil .

ORGANIC LETTERS, 2013, 15 (17) :4304-4307

[23] One-pot sequential C-N coupling and cross dehydrogenative couplings: synthesis of novel azole fused imidazo[1,2-a]pyridines [J].

Pericherla, Kasiviswanadharaju ;

Khedar, Poonam ;

Khungar, Bharti ;

Kumar, Anil .

CHEMICAL COMMUNICATIONS, 2013, 49 (28) :2924-2926

[24]

Pozharskii A.F., 1997, HETEROCYCLES LIFE SO, V1

[25] Mono and bis-6-arylbenzimidazo[1,2-c]quinazolines: A new class of antimicrobial agents [J].

Rohini, Rondla ;

Shanker, Kanne ;

Reddy, Puchakayala Muralidhar ;

Ho, Yen-Peng ;

Ravinder, Vadde .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (08) :3330-3339

[26] L-Proline: an efficient catalyst for the one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles [J].

Samai, Subhasis ;

Nandi, Ganesh Chandra ;

Singh, Pallavi ;

Singh, M. S. .

TETRAHEDRON, 2009, 65 (49) :10155-10161

[27] Copper-Mediated Amidation of Heterocyclic and Aromatic C-H Bonds [J].

Wang, Qiu ;

Schreiber, Stuart L. .

ORGANIC LETTERS, 2009, 11 (22) :5178-5180

[28] Catalytic Dehydrogenative Cross-Coupling: Forming Carbon-Carbon Bonds by Oxidizing Two Carbon-Hydrogen Bonds [J].

Yeung, Charles S. ;

Dong, Vy M. .

CHEMICAL REVIEWS, 2011, 111 (03) :1215-1292

[29] Copper-Catalyzed Domino Addition/Double Cyclization: An Approach to Polycyclic Benzimidazole Derivatives [J].

Yuan, Guodong ;

Liu, Haiquan ;

Gao, Jilong ;

Yang, Kangjian ;

Niu, Qingsheng ;

Mao, Hui ;

Wang, Xiaoxia ;

Lv, Xin .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (04) :1749-1757

[30] A Simple and Efficient Approach to the Synthesis of 2-Phenylquinazolines via sp3 C-H Functionalization [J].

Zhang, Jintang ;

Zhu, Dapeng ;

Yu, Chenmin ;

Wan, Changfeng ;

Wang, Zhiyong .

ORGANIC LETTERS, 2010, 12 (12) :2841-2843

← 1 2 3 →