Iron Catalyzed [3+2] Cycloaddition of Tetrahydroisoquinoline: Synthesis of Dihydropyrrolo[2,1-a]isoquinolines

被引：12

作者：

Liu, Si-Wei ^{[1
,2
]}

Ma, Dan-Dan ^{[1
]}

Zhu, Xin-Xin ^{[1
]}

Luo, Cheng-Dan ^{[1
]}

Tan, Hui-Lin ^{[1
]}

Ju, Xiao-Li ^{[1
]}

Tan, Xue ^{[1
]}

Tang, Xiao-Hui ^{[1
]}

Huang, Jie ^{[1
]}

Wang, Jia ^{[1
]}

Wang, Xian-Xun ^{[2
]}

Cui, Hai-Lei ^{[1
]}

机构：

[1] Chongqing Univ Arts & Sci, Lab Asymmetr Synth, 319 Honghe Ave, Chongqing 402160, Peoples R China

[2] Tonichem Pharmaceut Technol Co Ltd, Huizhou 516008, Peoples R China

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 9卷 / 10期

基金：

中国国家自然科学基金;

关键词：

Iron chloride; Dihydropyrrolo[2; 1-a]isoquinoline; Tetrahydroisoquinoline; Cycloaddition; Morita-Baylis-Hillman carbonate; BAYLIS-HILLMAN REACTION; EFFICIENT APPROACH; AZOMETHINE YLIDES; LAMELLARIN CORE; DERIVATIVES; CASCADE; CYCLIZATION; TANDEM; ANNULATION; REACTIVITY;

D O I：

10.1002/ajoc.202000211

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed an iron(III) chloride hexahydrate catalyzed formal [3+2] cycloaddition of tetrahydroisoquinolines with amide group-bearing Morita-Baylis-Hillman (MBH) carbonates. A range of highly functionalized dihydropyrrolo[2,1-a]isoquinolines could be prepared through SN2'/oxidation/electrocyclization/aromatization cascade (32-62% yield).

引用

页码：1617 / 1622

页数：6

共 50 条

[31] Regioselective Synthesis of Indolizines, Pyrrolo[2,1-a]isoquinolines, and Quinolines
Hashemi, Seyed Abolghasem
Khalili, Gholamhossein
SYNTHETIC COMMUNICATIONS, 2015, 45 (21) : 2491 - 2497
[32] Iron-catalyzed dimerization of pyrrolo[2,1-a]isoquinolines and pyrrolo [1,2-a]quinolines
Huang, Xiang
Li, Wan-Zhen
Pei, Shu-Chen
Cui, Hai -Lei
TETRAHEDRON LETTERS, 2023, 126
[33] Glycine-Based [3+2] Cycloaddition for the Synthesis of Pyrrolidine-Containing Polycyclic Compounds
Zhou, Tieli
Zhang, Xiaofeng
Zhan, Desheng
Zhang, Wei
MOLECULES, 2024, 29 (23):
[34] Synthesis of 5,6-dihydropyrrolo[2,1-a]isoquinolines via a TFA-promoted annulation of arylpropiolaldehydes and 1,2,3,4-tetrahydroisoquinolines
Zhang, Yage
Zhao, Wenyan
Hou, Guoquan
Liu, Li
Li, Jian
TETRAHEDRON LETTERS, 2023, 120
[35] TBAI/TBHP-catalyzed [3+2]cycloaddition/oxidation/aromatization cascade and online ESI-MS mechanistic studies: synthesis of pyrrolo[2,1-a] isoquinolines and indolizino[8,7-b]indoles
Nekkanti, Shalini
Kumar, Niggula Praveen
Sharma, Pankaj
Kamal, Ahmed
Nachtigall, Fabiane M.
Forero-Doria, Oscar
Santos, Leonardo S.
Shankaraiah, Nagula
RSC ADVANCES, 2016, 6 (04): : 2671 - 2677
[36] Synthesis of novel polyfunctional pyrrolo[2,1-a]isoquinolines based on 1,3-dipolar cycloaddition reactions
Bastrakov, M. A.
Starosotnikov, A. M.
RUSSIAN CHEMICAL BULLETIN, 2019, 68 (09) : 1729 - 1734
[37] Copper(I) Iodide Promoted [3+2]-Cycloaddition/Oxidation to Construct Pyrrolo[2,1-a ]isoquinolinoquinones from Naphthoquinones and Tetrahydroisoquinolines
Yu, Zihua
Tang, Xue
Huang, Chenxi
Shang, Yehan
Ye, Qing
Han, Liang
Li, Yujin
SYNLETT, 2022, 33 (06) : 563 - 568
[38] A DFT study on the mechanism and selectivity of [3+2] cycloaddition reactions leading to pyrole[2,1-a] phthalazine compounds
Lotfi, Marjan
Hamzehloueian, Mahshid
Haghdadi, Mina
THEORETICAL CHEMISTRY ACCOUNTS, 2021, 140 (05)
[39] Visible-Light-Catalyzed Formal [3+2] Annulation-Aromatization of Amidines with Isoquinolinium N-Ylides: Access to Imidazo[2,1-a]isoquinolines
Zheng, Lvyin
Zou, Xiaoying
Yang, Xiaojuan
Deng, Lei
Guo, Wei
ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (21) : 3629 - 3636
[40] Copper-Catalyzed Tandem Synthesis of Indolo-, Pyrrolo[2,1-a]isoquinolines, Naphthyridines and Bisindolo/Pyrrolo[2,1-a]isoquinolines via Hydroamination of ortho-Haloarylalkynes Followed by C-2 Arylation
Verma, Akhilesh K.
Jha, Rajeev R.
Chaudhary, Ritu
Tiwari, Rakesh K.
Reddy, Kotla Siva K.
Danodia, Abhinandan
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (18) : 8191 - 8205

← 1 2 3 4 5 →