Synthesis of Optically Active 2H-Thiopyrano[2,3-b]quinolines with Three Contiguous Stereocenters via an Organocatalytic Asymmetric Tandem Michael-Henry Reaction

被引：64

作者：

Wu, Lulu ^{[1
]}

Wang, Youming ^{[1
]}

Song, Haibin ^{[1
]}

Tang, Liangfu ^{[1
]}

Zhou, Zhenghong ^{[1
]}

Tang, Chuchi ^{[1
]}

机构：

[1] Nankai Univ, Inst Elementoorgan Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2013年 / 355卷 / 06期

基金：

中国国家自然科学基金;

关键词：

Henry reaction; Michael addition; nitrooelfins; tandem reactions; 2H-thiopyrano[2; 3-b]quinolines; ALDOL REACTIONS; SUPPORTED SYNTHESIS; QUINOLINES; ANTAGONISTS; BINDING; SERIES;

D O I：

10.1002/adsc.201300086

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Optically active 2H-thiopyrano[2,3-b]quinolines with three contiguous stereocenters have been synthesized via a chiral bifunctional squaramide-catalyzed tandem MichaelHenry reaction between 2-mercaptoquinoline-3-carbaldehydes and nitroolefins. The reactions proceed with excellent diastereo- and enantioselectivity to give the title compounds in high yields with high levels of diastereo- and enantioselectivity (up to >99/1 dr and >99% ee, respectively).

引用

页码：1053 / 1057

页数：5

共 50 条

[21] A facile synthesis of pyrrolo[2,3-b]quinolines via a Rh(I)-catalyzed carbodiimide-Pauson-Khand-type reaction
Saito, Takao
Furukawa, Naoki
Otani, Takashi
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (05) : 1126 - 1132
[22] Organocatalytic asymmetric synthesis of both cis- and trans-configured pyrano[2,3-b]chromenes via different dehydration pathways
Lv, Xue-Jiao
Zhao, Wei-Wei
Chen, Ying-Han
Wan, Sheng-Biao
Liu, Yan-Kai
ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (12): : 1972 - 1976
[23] First construction of 12H-thiochromeno[2,3-b]quinolines and 5H-benzo[7,8] thiocino-[2,3-b]quinolines via intramolecular Friedel-Crafts reaction of Morita-Baylis-Hillman adducts
Zhong, Weihui
Ma, Wang
Liu, Yanbin
TETRAHEDRON, 2011, 67 (19) : 3509 - 3518
[24] Enantio- and diastereoselective synthesis of tetrahydrofuro[2,3-b]furan-2(3H)-one derivatives and related oxygen heterocycles via an asymmetric organocatalytic cascade process
Zhao, Wei-Wei
Liu, Yan-Kai
ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (12): : 2358 - 2363
[25] Facile one-pot, three-component synthesis of novel bis(heterocycles) incorporating thieno[2,3-b]thiophenes via Michael addition reaction
Eid, Elshimaa M.
Hassaneen, Huwaida M. E.
Abdelhamid, Ismail A.
Elwahy, Ahmed H. M.
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2020, 57 (05) : 2243 - 2255
[26] Synthesis of isomeric 4-(N-methyltetrazolylamino)-2-phenyl-4H-thiopyrano[2,3-b]quinoline-3-carbaldehydes and 4-hydroxy-2-phenyl-4H-thiopyrano[2,3-b]quinoline-3-carbaldehyde based on tandem thiol-Michael and (aza)-Morita–Baylis–Hillman reactions and an in vitro study of the activity of the obtained compounds against influenza virus
Andrey V. Khramchikhin
Mariya А. Skryl’nikova
Yuliya N. Pavlyukova
Vladimir V. Zarubaev
Yana L. Esaulkova
Anna А. Muryleva
Nadezhda T. Shmanyova
Gevorg G. Danagulyan
Vladimir А. Ostrovskii
Chemistry of Heterocyclic Compounds, 2022, 58 : 267 - 270
[27] Chiral bifunctional squaramide catalyzed asymmetric tandem Michael-cyclization reaction: efficient synthesis of optically active 2-amino-4H-chromene-3-carbonitrile derivatives
Hu, Keling
Lu, Aidang
Wang, Youming
Zhou, Zhenghong
Tang, Chuchi
TETRAHEDRON-ASYMMETRY, 2013, 24 (15-16) : 953 - 957
[28] Enantioselective synthesis of spiro[indoline-3,4′-pyrano[2,3-c]pyrazole] derivatives via an organocatalytic asymmetric Michael/cyclization cascade reaction
Xie, Jin
Xing, Xiao-Yu
Sha, Feng
Wu, Zhi-Yan
Wu, Xin-Yan
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (35) : 8346 - 8355
[29] The stereoselective synthesis of tetrahydrothiopyrano[2,3-b]indole skeletons via tandem reaction of indoline-2-thiones to Baylis-Hillman adduct acetates
Moghaddam, Firouz Matloubi
Foroushani, Behzad Koushki
Sobhani, Maryam
Masoud, Nazila
Khodabakhshi, Mohammad Reza
Weng, Ng Seik
TETRAHEDRON, 2013, 69 (38) : 8169 - 8173
[30] Synthesis of isomeric 4-(N-methyltetrazolylamino)-2-phenyl-4H-thiopyrano[2,3-b]quinoline-3-carbaldehydes and 4-hydroxy-2-phenyl-4H-thiopyrano[2,3-b]quinoline-3-carbaldehyde based on tandem thiol-Michael and (aza)-Morita-Baylis-Hillman reactions and an in vitro study of the activity of the obtained compounds against influenza virus
Khramchikhin, Andrey V.
Skryl'nikova, Mariya A.
Pavlyukova, Yuliya N.
Zarubaev, Vladimir V.
Esaulkova, Yana L.
Muryleva, Anna A.
Shmanyova, Nadezhda T.
Danagulyan, Gevorg G.
Ostrovskii, Vladimir A.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2022, 58 (4-5) : 267 - 270

← 1 2 3 4 5 →