Alkylamino-Directed One-Pot Reaction of N-Alkyl Anilines with CO, Amines and Aldehydes Leading to 2,3-Dihydroquinazolin-4(1H)-ones

被引：22

作者：

Zhang, Xiaopeng ^{[1
]}

Li, Zhengwei ^{[1
]}

Ding, Qianqian ^{[1
]}

Li, Xiaochuan ^{[1
]}

Fan, Xuesen ^{[1
]}

Zhang, Guisheng ^{[1
]}

机构：

[1] Henan Normal Univ, Collaborat Innovat Ctr Henan Prov Green Mfg Fine, Sch Chem & Chem Engn,Key Lab Green Chem Media & R, Henan Key Lab Organ Funct Mol & Drug Innovat,Mini, Xinxiang 453007, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2019年 / 361卷 / 05期

基金：

中国国家自然科学基金;

关键词：

C-H activation; 2,3-dihydroquinazolin-4(1H)-ones; embedded directing group; N-alkyl anilines; palladium; BIOLOGICAL EVALUATION; ASYMMETRIC-SYNTHESIS; CATALYZED SYNTHESIS; MEDIATED SYNTHESIS; BOND ACTIVATION; H BONDS; DERIVATIVES; DESIGN; FUNCTIONALIZATION; CARBONYLATION;

D O I：

10.1002/adsc.201801267

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An economical and efficient approach to pharmaceutically and biologically significant 2,3-dihydroquinazolin-4(1H)-ones has been disclosed. The one-pot multicomponent reaction was performed through a palladium-catalyzed ortho-selective oxidative carbonylation of N-substituted anilines with CO and primary amines, and subsequent condensation with aldehydes in MeCN by using alkylamino as the directing group, KI/AcOH as the additives, and Cu(OAc)(2) as the oxidant. This intriguing straightforward method features embedded directing strategy, simple starting materials, mild conditions, high atom/step economic economy, broad substrate scope and good product diversity.

引用

页码：976 / 982

页数：7

共 50 条

[21] Inclusion complex of Isatoic anhydride with β-cyclodextrin and supramolecular one-pot synthesis of 2, 3-dihydroquinazolin-4(1H)-ones in aqueous media
Patil, Dipak R.
Ingole, Pravin G.
Singh, Kripal
Dalal, Dipak S.
[J]. JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2013, 76 (3-4) : 327 - 332
[22] Efficient one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones from aromatic aldehydes and their one-pot oxidation to quinazolin-4(3H)-ones catalyzed by Bi(NO3)3•5H2O: Investigating the role of the catalyst
Mohammadpoor-Baltork, Iraj
Khosropour, Ahmad R.
Moghadam, Majid
Tangestaninejad, Shahram
Mirkhani, Valiollah
Baghersad, Saeid
Mirjafari, Arsalan
[J]. COMPTES RENDUS CHIMIE, 2011, 14 (10) : 944 - 952
[23] Three-component one-pot metal-free synthesis of 2,3-dihydroquinazolin-4(1H)-ones using Mukaiyama's reagent
Kumar, Ashish
Gupta, Monika
Rajput, Chatrasal S.
[J]. ARKIVOC, 2023,
[24] Green and One-Pot Three-Component Synthesis of 2,3-Dihydroquinazolin-4(1H)-Ones Promoted by Citric Acid as Recoverable Catalyst in Water
Ghorbani-Choghamarani, Arash
Taghipour, Tahereh
[J]. LETTERS IN ORGANIC CHEMISTRY, 2011, 8 (07) : 470 - 476
[25] An ionic liquid catalyzed reusable protocol for one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-one under mild conditions
Nagarajan, S.
Shaikh, Tanveer Mahamadali
Kandasamy, Elango
[J]. NEW JOURNAL OF CHEMISTRY, 2015, 39 (12) : 9693 - 9699
[26] 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
Zhang, Xiaopeng
Pang, Qiuyang
Liu, Dan
Guo, Zhenhua
Zhang, Guisheng
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (14) : 2791 - 2796
[27] KCC-1/Pr-SO3H: an efficient heterogeneous catalyst for green and one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-one
Azizi, Sajjad
Soleymani, Jafar
Hasanzadeh, Mohammad
[J]. NANOCOMPOSITES, 2020, 6 (01) : 31 - 40
[28] Recyclable [Ce(L-Pro)2]2 (Oxa) used as Heterogeneous Catalyst: One-Pot Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones in Ethanol
Katla, Ramesh
Chowrasia, Rakhi
da Silva, Caren D. G.
de Oliveira, Aline R.
dos Santos, Beatriz F.
Domingues, Nelson L. C.
[J]. SYNTHESIS-STUTTGART, 2017, 49 (23): : 5143 - 5148
[29] Synthesis and Antibacterial Evaluation of New developed 2,3-Dihydroquinazolin-4(1H)-ones
Emam, Aya M.
Kothayer, Hend
Ibrahim, Samy M.
El-Sadek, Mohamed
[J]. EGYPTIAN JOURNAL OF CHEMISTRY, 2022, 65 (13): : 1547 - 1551
[30] 2-(2-Chlorophenyl)-2,3-dihydroquinazolin-4(1H)-one
Li, Ming-Jian
Feng, Chang-Jun
[J]. ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O2145 - U1949

← 1 2 3 4 5 →