Hydrogen-Bond-Catalyzed Arylationof 3-(Aminoalkyl)indoles via C-N Bond Cleavage with Thiourea under Microwave Irradiation: An Approach to 3-(α,α-Diarylmethyl) indoles

被引：24

作者：

Deb, Mohit L. ^{[1
]}

Das, Churnika ^{[1
]}

Deka, Bhaskar ^{[1
]}

Saikia, Prakash J. ^{[2
]}

Baruah, Pranjal K. ^{[1
]}

机构：

[1] Gauhati Univ, Dept Appl Sci, GUIST, Gauhati 781014, Assam, India

[2] Analyt Chem Div CSIR NEIST, Jorhat 785006, Assam, India

来源：

SYNLETT | 2016年 / 27卷 / 20期

关键词：

hydrogen-bond-catalyzed; thiourea; microwave; indoles; vinylogous iminium ion; 3-AMINO ALKYLATED INDOLES; MANNICH-TYPE REACTION; MULTICOMPONENT SYNTHESIS; ANTIOXIDANT ACTIVITIES; MICHAEL ADDITION; DERIVATIVES; CHEMISTRY;

D O I：

10.1055/s-0036-1588887

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed a simple and efficient method for the arylation of 3-(aminoalkyl) indoles with aryl alcohols and other aromatic nucleophiles through C-N bond cleavage under microwave irradiation to synthesize 3-(alpha, alpha-diarylmethyl) indoles. The method uses thiourea as catalyst, which is environmentally benign, water-tolerant and easy to handle. Notably, acid-sensitive substrates are tolerated under the reaction conditions. Thiourea activates the tertiary amine through double hydrogen bonding and converts it into a better leaving group. The reaction proceeds through the formation of vinylogous iminium ion as an intermediate.

引用

页码：2788 / 2794

页数：7

共 50 条

[31] Selective Synthesis of Pyrano[3,2-b]indoles or Cyclopenta[b]indoles Tethered with Medium-Sized Rings via Cascade C-C σ-Bond Cleavage and C-H Functionalization
Wang, Mengdan
Yang, Yajie
Yin, Liqiang
Feng, Ye
Li, Yanzhong
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (01): : 683 - 692
[32] Vicinal diphosphorylation of enaminones with diaryl phosphine oxides via AlCl3-mediated C-N bond cleavage
Jin, Xin
An, Yong
Chen, Jia
Wang, Xianheng
Wang, Huabin
Zhao, Changkuo
Huang, Qiang
TETRAHEDRON LETTERS, 2025, 158
[33] Domino C-S/C-N Bond Formation using Well-Defined Copper-Phosphine Complex Catalyst: Divergent Approach to 3-Sulfenylated Indoles
Tamargo, Ramuel John Inductivo
Kim, Sung Hong
Lee, Yong Rok
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (17) : 4005 - 4015
[34] PALLADIUM-CATALYZED DIRECT ARYLATION AND ALKENYLATION OF 3-(INDOL-3-YL)PROPIONIC ACIDS THROUGH C-H BOND CLEAVAGE
Takeda, Daisuke
Hirano, Koji
Satoh, Tetsuya
Miura, Masahiro
HETEROCYCLES, 2014, 88 (01) : 275 - 286
[35] Rapid access to 3-(N-substituted)-aminoquinolin-2(1H)-ones using palladium-catalyzed C-N bond coupling reaction
Messaoudi, Samir
Audisio, Davide
Brion, Jean-Daniel
Alami, Mouad
TETRAHEDRON, 2007, 63 (41) : 10202 - 10210
[36] A new synthetic approach to pyrrolo[3,2-b]indoles via regioselective formation of pyrrole and intramolecular C-N coupling
Karkhelikar, Manjusha V.
Rao, Vijay V.
Shinde, Sundar S.
Likhar, Pravin R.
TETRAHEDRON LETTERS, 2016, 57 (43) : 4803 - 4806
[37] Co-Catalyzed C(sp3)-C(sp2) bond cleavage via hydrogen atom transfer
Zhou, Bingqing
Tian, Di
An, Jinglin
Zhou, Yalan
Yan, Rui
Song, Hao
Liu, Xiao-Yu
Qin, Yong
ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (08) : 2135 - 2140
[38] Molecular Iodine-Catalyzed Sulfonyl-Activated sp3 C-N Bond Cleavage for the C3-Alkylation of 4-Hydroxycoumarins
Zhao, Jinyu
Jia, Lina
Yuan, Changping
Li, Linlin
Hu, Minggang
Han, Fuzhong
Hu, Xiangping
CHEMISTRYSELECT, 2022, 7 (09):
[39] Sc(OTf)3-Catalyzed Domino C-C/C-N Bond Formation of Aziridines with Quinones via Radical Pathway
Verma, Kshitiz
Mishra, Manmath
Maharana, Prabhat Kumar
Bhattacharyya, Hemanga
Saha, Sharajit
Punniyamurthy, Tharmalingam
ORGANIC LETTERS, 2023, 25 (43) : 7933 - 7938
[40] Rh/Cu-catalyzed multiple C-H, C-C, and C-N bond cleavage: facile synthesis of pyrido[2,1-a]indoles from 1-(pyridin-2-yl)-1H-indoles and γ-substituted propargyl alcohols
Li, Ting
Wang, Zhen
Zhang, Mingliang
Zhang, Hui-Jun
Wen, Ting-Bin
CHEMICAL COMMUNICATIONS, 2015, 51 (31) : 6777 - 6780

← 1 2 3 4 5 →