Diastereoselective Synthesis of Spiropyrazolones via 1,3-Dipolar [3+2] Cycloadditions between Pyrazolone-Based Olefins and N,N′-Cyclic Azomethine Imines

被引：4

作者：

Tang, Zhe ^{[1
]}

Wu, Hui-Hui ^{[1
]}

Xiao-Zu Fan ^{[1
]}

Zhang, Heng ^{[1
]}

Cai, Lu-Yu ^{[1
]}

Bi, Xiao-Fan ^{[1
]}

Zhao, Hong-Wu ^{[1
]}

机构：

[1] Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing Key Lab Environm & Viral Oncol, 100 Pingleyuan, Beijing 100124, Peoples R China

来源：

SYNLETT | 2021年 / 32卷 / 12期

关键词：

1,3-dipolar [3+2] cycloaddition; pyrazolone-based olefin; N; N '-cyclic azomethine imine; spiropyrazolone; diastereoselectivity; SPIROCYCLIC PYRAZOLONE; ASYMMETRIC-SYNTHESIS; ANNULATION REACTION; CONSTRUCTION;

D O I：

10.1055/a-1506-4509

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Under the catalysis of PhCO2H, the 1,3-dipolar [3+2] cycloaddition between pyrazolone-based olefins and N,N'-cyclic azomethine imines proceeded readily, thus delivering structurally novel spiropyrazolones with up to 98% yield and >20:1 dr. The relative stereochemical configuration of the obtained spiropyrazolones was unambiguously assigned by X-ray single-crystal structure analysis. The diastereoselective formation of the title spiropyrazolones was interpreted by the hypothesized reaction mechanism.

引用

页码：1201 / 1206

页数：6

共 50 条

[41] Isatin N,N′-Cyclic Azomethine Imine 1,3-Dipole and Abnormal [3+2]-Cycloaddition with Maleimide in the Presence of 1,4-Diazabicyclo[2.2.2]octane
Wang, Xiao
Yang, Peng
Zhang, Yong
Tang, Chao-Zhe
Tian, Fang
Peng, Lin
Wang, Li-Xin
ORGANIC LETTERS, 2017, 19 (03) : 646 - 649
[42] [3+2] cycloaddition reaction of N,N′ cyclic azomethine imines toward highly electron-deficient nitroalkenes: A molecular electron density theory study
Babazadeh, Sayyed Mohsen
Emamian, Saeedreza
Zahedi, Ehsan
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2019, 32 (05)
[43] Synthesis and biological activity of potential antiviral compounds through 1,3-dipolar cycloadditions. Part 2: nitrones, nitrile oxides and imines, and other 1,3-dipoles
Faita, Giuseppe
Mella, Mariella
Quadrelli, Paolo
ARKIVOC, 2022, : 257 - 294
[44] Highly diastereoselective synthesis of imidazolidine-dispirooxindoles via three-component [3+2] cycloadditions of isatins, 2-(aminomethyl)pyridine and isatin-based imines
Zhao, Hong-Wu
Chen, Xiao-Qin
Yang, Zhao
Tian, Ting
Li, Bo
Meng, Wei
Song, Xiu-Qing
Pang, Hai-Liang
RSC ADVANCES, 2015, 5 (125): : 103116 - 103122
[45] Synthesis of pyrrolidin-2-ylidenes and pyrrol-2-ylidenes via 1,3-dipolar cycloaddition of H-bond-assisted azomethine ylides to nitrostyrenes
Yavari, Issa
Mohsenzadeh, Ramin
Ravaghi, Parisa
Safaei, Maryam
ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (25) : 5265 - 5273
[46] Enantioselective Synthesis of Chiral Imidazolidine Derivatives by Asymmetric Silver/Xing-Phos-Catalyzed Homo-1,3-Dipolar [3+2] Cycloaddition of Azomethine Ylides
Yu, Bo
Bai, Xing-Feng
Lv, Ji-Yuan
Yuan, Yang
Cao, Jian
Zheng, Zhan-Jiang
Xu, Zheng
Cui, Yu-Ming
Yang, Ke-Fang
Xu, Li-Wen
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (20) : 3577 - 3584
[47] Catalytic Asymmetric 1,3-Dipolar Cycloadditions of Alkynes with Isatin-Derived Azomethine Ylides: Enantioselective Synthesis of Spiro[indoline-3,2′-pyrrole] Derivatives
Shi, Feng
Zhu, Ren-Yi
Liang, Xia
Tu, Shu-Jiang
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (11-12) : 2447 - 2458
[48] Syntheses of spiro[indazole-3,3′-indolin]-2′-ones and spiro[indazole-3,3′-indolin]-2′-imines via 1,3-dipolar cycloadditions of arynes and studies on their isomerization reactions
Cheng, Bin
Li, Yuntong
Zu, Bing
Wang, Taimin
Wang, Renqi
Li, Yun
Zhai, Hongbin
TETRAHEDRON, 2019, 75 (52)
[49] [3+2] Cycloadditions of Tertiary Amine N-Oxides and Silyl Imines as an Innovative Route to 1,2-Diamines
Hejnosz, Sarah L.
Beres, Danielle R.
Cocolas, Alexander H.
Neal, Martin J.
Musiak, Benjamin S.
Hanna, Marianne M. B.
Bloomfield, Aaron J.
Montgomery, Thomas D.
ORGANIC LETTERS, 2023, 25 (25) : 4638 - 4643
[50] R-BINOL-Chiral Phosphoric Acid Catalyzed Regioselective Synthesis of 7-Oxo-Pyrazolo[1,2-a]Pyrazoles via [3+2] Cycloaddition Reaction of Morita Baylis Hillman Adducts with N, N'-Cyclic Azomethine Imines
Karthikeyan, S.
Choppella, Sairathna
Murali, Anna Chandrasekar
Subimol, K. R.
Monica, J. Helen Ratna
Ravva, Mahesh Kumar
Kumar Ayyanoth, Karthik Krishna
CHEMISTRYSELECT, 2024, 9 (27):

← 1 2 3 4 5 →