Pd(<sc>ii</sc>)-catalyzed cascade annulation of N-substituted anilines with CO, NH4OAc and aldehydes to N1-substituted 2,3-dihydroquinazolin-4(1H)-ones

被引：0

作者：

Zhang, Xiaopeng ^{[1
]}

Pang, Qiuyang ^{[1
]}

Liu, Dan ^{[1
]}

Guo, Zhenhua ^{[1
]}

Zhang, Guisheng ^{[1
]}

机构：

[1] Henan Normal Univ, Sch Chem & Chem Engn, Key Lab Green Chem Media & React,, Key Lab Green Chem Media & React,NMPA Key Lab Res, Xinxiang 453007, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2024年 / 22卷 / 14期

基金：

中国国家自然科学基金;

关键词：

CATALYZED ORTHO-ARYLATION; OXIDATIVE CARBONYLATION; H FUNCTIONALIZATION; CRYSTAL-STRUCTURE; ALKYL ANILINES; SIMPLE ARENES; 4(1H)-QUINAZOLINONES; QUINAZOLINONES; DERIVATIVES; AMINES;

D O I：

10.1039/d4ob00055b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile and direct approach to N1-substituted 2,3-dihydroquinazolin-4(1H)-ones has been developed via Pd(ii)-catalyzed one-pot cascade annulation of N-substituted anilines with CO, NH4OAc and aldehydes, and it features an intrinsic directing strategy, cheap and easily obtainable raw materials, low cost, high step economy and efficiency, broad substrate scope and good product diversity. This protocol has been successfully applied to the synthesis of glycozolone A and gram-level experiments. Based on the control experiments and the literature, the reaction mechanism was proposed.

引用

页码：2791 / 2796

页数：6

共 36 条

[1] Metal-catalysed C-H bond activation and borylation
Bisht, Ranjana
Haldar, Chabush
Hassan, Mirja Md Mahamudul
Hoque, Md Emdadul
Chaturvedi, Jagriti
Chattopadhyay, Buddhadeb
[J]. CHEMICAL SOCIETY REVIEWS, 2022, 51 (12) : 5042 - 5100
[2] Removal and modification of directing groups used in metal-catalyzed C-H functionalization: the magical step of conversion into 'conventional' functional groups
Carvalho, Renato L.
Almeida, Renata G.
Murali, Karunanidhi
Machado, Luana A.
Pedrosa, Leandro F.
Dolui, Pravas
Maiti, Debabrata
Silva Junior, Eufranio N.
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (03) : 525 - 547
[3] Multicomponent reactions and photo/electrochemistry join forces: atom economy meets energy efficiency
Coppola, Guglielmo A.
Pillitteri, Serena
Van der Eycken, Erik V.
You, Shu-Li
Sharma, Upendra K.
[J]. CHEMICAL SOCIETY REVIEWS, 2022, 51 (06) : 2313 - 2382
[4] Synthesis, biological screening, and molecular docking of quinazolinone and quinazolinethione as phosphodiesterase 7 inhibitors
Elfeky, Sherin M.
Sobahi, Tariq R.
Gineinah, Magdy M.
Ahmed, Nesreen S.
[J]. ARCHIV DER PHARMAZIE, 2020, 353 (01)
[5] AN EFFICIENT AND SELECTIVE PALLADIUM-CATALYZED OXIDATIVE DICARBONYLATION OF ALKYNES TO ALKYL-MALEIC OR ARYL-MALEIC ESTERS
GABRIELE, B
COSTA, M
SALERNO, G
CHIUSOLI, GP
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (01): : 83 - 87
[6] C-H functionalization of quinazolinones by transition metal catalysis
Ghosh, Prasanjit
Ganguly, Bhaskar
Das, Sajal
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (24) : 4497 - 4518
[7] Palladium-Catalyzed Regioselective Carbonylation of C-H Bonds of N-Alkyl Anilines for Synthesis of Isatoic Anhydrides
Guan, Zheng-Hui
Chen, Ming
Ren, Zhi-Hui
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (42) : 17490 - 17493
[8] Recent advances in transition-metal-catalyzed carbene insertion to C-H bonds
He, Yuan
Huang, Zilong
Wu, Kaikai
Ma, Juan
Zhou, Yong-Gui
Yu, Zhengkun
[J]. CHEMICAL SOCIETY REVIEWS, 2022, 51 (07) : 2759 - 2852
[9] Oxidative carbonylation of glycerol to glycerol carbonate catalyzed by PdCl2(phen)/KI
Hu, Jianglin
Li, Jinjin
Gu, Yanlong
Guan, Zhenhong
Mo, Wanling
Ni, Youming
Li, Tao
Li, Guangxing
[J]. APPLIED CATALYSIS A-GENERAL, 2010, 386 (1-2) : 188 - 193
[10] Synthesis of polyheterocycles via multicomponent reactions
Ibarra, Ilich A.
Islas-Jacome, Alejandro
Gonzalez-Zamora, Eduardo
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (09) : 1402 - 1418

← 1 2 3 4 →