A metal-free aromatic cascade for the synthesis of diverse heterocycles

被引：10

作者：

Schlitzer, Steven C. ^{[1
,2
]}

Arunprasath, Dhanarajan ^{[1
,2
]}

Stevens, Katelyn G. ^{[1
,2
]}

Sharma, Indrajeet ^{[1
,2
]}

机构：

[1] Univ Oklahoma, Dept Chem & Biochem, 101 Stephenson Pkwy, Norman, OK 73071 USA

[2] Univ Oklahoma, Inst Nat Prod Applicat & Res Technol, 101 Stephenson Pkwy, Norman, OK 73071 USA

来源：

ORGANIC CHEMISTRY FRONTIERS | 2020年 / 7卷 / 07期

关键词：

STEREOSELECTIVE-SYNTHESIS; ELECTROCYCLIC REACTIONS; KETENES; REACTIVITY; CATALYSIS; ANALOGS; YLIDES; ACCESS; STILLE;

D O I：

10.1039/c9qo01336a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A metal-free aromatic cascade has been developed for the synthesis of diverse heterocycles from readily accessible hydroxy/aminochalcones and acid/alkyl halides. The cascade is initiated by a base-mediated intramolecular aldol cyclization/dehydration sequence to provide a triene, which sets the stage for a 6 pi-electrocyclization/oxidative aromatization to access diverse heterocyclic scaffolds.

引用

页码：913 / 918

页数：6

共 50 条

[41] Metal-Free Reduction of Aromatic Nitro Compounds to Aromatic Amines with B2pin2 in Isopropanol [J].

Lu, Hongtao ;

Geng, Zhiyue ;

Li, Jingya ;

Zou, Dapeng ;

Wu, Yusheng ;

Wu, Yangjie .

ORGANIC LETTERS, 2016, 18 (11) :2774-2776

[42] Metal-free Oxidative Coupling of Aromatic Alkenes with Thiols Leading to (E)-Vinyl Sulfones [J].

Wang, Leilei ;

Yue, Huilan ;

Yang, Daoshan ;

Cui, Huanhuan ;

Zhu, Minghui ;

Wang, Jinming ;

Wei, Wei ;

Wang, Hua .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (13) :6857-6864

[43] An Unprecedented, Lewis Acid-Mediated, Metal-Free Iodoannulation Strategy to Aromatic Iodides [J].

Banik, Trisha ;

Betkekar, Vipul V. ;

Kaliappan, Krishna P. .

CHEMISTRY-AN ASIAN JOURNAL, 2018, 13 (23) :3676-3680

[44] Diverse reactions of S-S function under metal-mediated and metal-free thermolysis conditions [J].

Zhu, Hai-Bin ;

Li, Lei ;

Wang, Hai ;

Lu, Xin ;

Gou, Shao-Hua .

INORGANIC CHEMISTRY COMMUNICATIONS, 2010, 13 (01) :30-32

[45] Metal-free multicomponent reactions: a benign access to monocyclic six-membered N-heterocycles [J].

Preeti ;

Singh, Krishna Nand .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (12) :2622-2657

[46] Acyl Radicals from α-Keto Acids: Metal-Free Visible-Light-Promoted Acylation of Heterocycles [J].

Zhu, Hu-Lin ;

Zeng, Fan-Lin ;

Chen, Xiao-Lan ;

Sun, Kai ;

Li, Hao-Cong ;

Yuan, Xiao-Ya ;

Qu, Ling-Bo ;

Yu, Bing .

ORGANIC LETTERS, 2021, 23 (08) :2976-2980

[47] Metal-Free Trifluoromethylation of Indazoles [J].

Ghosh, Payel ;

Mondal, Susmita ;

Hajra, Alakananda .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (21) :13618-13623

[48] Metal-free alkynylsulfonylation of vinylarenes [J].

Wang, Fei ;

Zhou, Huan ;

Li, Yajun ;

Bao, Hongli .

ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (08) :1817-1822

[49] Synthesis of Saturated N-Heterocycles via a Catalytic Hydrogenation Cascade [J].

Wagener, Tobias ;

Pierau, Marco ;

Heusler, Arne ;

Glorius, Frank .

ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (19) :3366-3371

[50] Converting waste PET into dimethyl terephthalate and diverse boronic esters under metal-free conditions [J].

Zhang, Minghao ;

Yu, Yunkai ;

Wang, Zhuo ;

Zhang, Shaoyu ;

Gao, Xiong ;

Liu, Jiaming ;

Li, Jing ;

Wu, Weixiang ;

Mei, Qingqing .

GREEN CHEMISTRY, 2024, 26 (22) :11132-11139

← 1 2 3 4 5 →