Base-promoted tandem synthesis of 2-azaaryl indoline

被引：0

作者：

Chen, Shuguang ^{[1
]}

Tan, Jiahong ^{[1
]}

Wu, Hao ^{[1
]}

Zhao, Quansheng ^{[1
]}

Shang, Yongjia ^{[1
]}

机构：

[1] Anhui Normal Univ, Coll Chem & Mat Sci, Key Lab Funct Mol Solids, Anhui Lab Mol Based Mat,Minist Educ,State Key Lab, Wuhu 241000, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2023年 / 21卷 / 46期

基金：

中国国家自然科学基金;

关键词：

DERIVATIVES; ANTIOXIDANT; ANTICANCER; LIGANDS; DESIGN;

D O I：

10.1039/d3ob01444d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel tandem method to synthesize 2-azaaryl indoline promoted by LiN(SiMe3)2 from 2-azaaryl methyl amine and 2-fluoro benzyl bromides was developed. Mechanistic investigation indicated that this tandem cyclization was initiated by selective benzyl C-SN2 substitution followed by an intramolecular SNAr reaction. Diverse 2-azaaryl indoles could also be obtained via simple functional transformations. A novel strategy involving base-promoted tandem SN2 substitution and intramolecular SNAr addition from 2-azaaryl methyl amine and ortho-fluoro benzyl bromide was designed.

引用

页码：9133 / 9137

页数：5

共 50 条

[31] Base-Promoted α-Alkylation of Arylacetonitriles with Alcohols
Roy, Bivas Chandra
Ansari, Istikhar A.
Samim, Sk. Abdus
Kundu, Sabuj
CHEMISTRY-AN ASIAN JOURNAL, 2019, 14 (13) : 2215 - 2219
[32] MECHANISM OF BASE-PROMOTED CYCLODIMERIZATION OF CYCLOHEPTATRIENE
STALEY, SW
ORVEDAL, AW
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (05) : 1618 - 1620
[33] Synthesis and acid- and base-promoted ring opening of polycarbocyclic oxiranes
Marchand, AP
Dong, EZ
Bott, SG
TETRAHEDRON, 1998, 54 (18) : 4459 - 4470
[34] Selective base-promoted synthesis of substituted selenophenes by carbocyclization of (Z)-benzylselenoenynes
Barancelli, Daniela A.
Acker, Carmine I.
Menezes, Paulo H.
Zeni, Gilson
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (05) : 1529 - 1537
[35] BASE-PROMOTED REARRANGEMENT OF 2,3-EPOXYCYCLOHEXANONES TO PHENOIS
BELLESIA, F
GHELFI, F
GRANDI, R
PAGNONI, UM
JOURNAL OF CHEMICAL RESEARCH-S, 1985, (12): : 400 - 401
[36] ORIENTATION IN BASE-PROMOTED DEHYDROCHLORINATION OF 2,2,3-TRICHLOROBUTANE
BARTSCH, RA
CROFT, AP
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (07): : 1364 - 1365
[37] Base-promoted synthesis of diarylsulfones from sulfonyl hydrazines and diaryliodonium salts
Gong, Bozhen
Zhu, Haibo
Yang, Liu
Wang, Haifeng
Fan, Qiangwen
Xie, Zongbo
Le, Zhanggao
ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (17) : 3501 - 3505
[38] Base-promoted solid-phase synthesis of substituted hydantoins and thiohydantoins
Matthews, J
Rivero, RA
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17): : 6090 - 6092
[39] An unexpected base-promoted isomerization of oxazolinylaryl oxiranes: synthesis of oxazolinylaryl alkanones
Perna, FM
Capriati, V
Florio, S
Luisi, R
TETRAHEDRON LETTERS, 2002, 43 (43) : 7739 - 7742
[40] A novel base-promoted cyclization: synthesis of substituted benzo[b]furans
Damera, Krishna
Ke, Bowen
Wang, Ke
Dai, Chaofeng
Wang, Lifang
Wang, Binghe
RSC ADVANCES, 2012, 2 (25): : 9403 - 9405

← 1 2 3 4 5 →