Synthesis of 2-aminochromene derivatives from 1-(2-imino-2H-chromen-3-yl)pyridin-1-ium perchlorates and nitromethane in basic medium

被引：2

作者：

Storozhenko, Olga A. ^{[1
]}

Yue, Xiaoyi ^{[1
]}

Festa, Alexey A. ^{[1
]}

Varlamov, Alexey A. ^{[1
]}

Voskressensky, Leonid G. ^{[1
]}

机构：

[1] RUDN Univ, 6 Miklukho Maklaya St, Moscow 117198, Russia

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2020年 / 56卷 / 09期

基金：

俄罗斯基础研究基金会;

关键词：

2-aminochromene; 2-iminochromene; nitromethane; beta-elimination; Michael addition; ONE-POT; HIGHLY EFFICIENT; MULTICOMPONENT REACTIONS; CATALYST; 2-AMINO-4H-CHROMENES; PYRIMIDINE; CHROMENES; SOLVENT;

D O I：

10.1007/s10593-020-02793-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel 2-amino-4-(nitromethylidene)chromenes were obtained as a result of the reaction of 1-(2-imino-2H-chromen-3-yl)pyridinium perchlorates and nitromethane by the action of DBU at reflux in trifluoroethanol. The starting 2-iminochromenes are readily accessible from the corresponding salicylic aldehydes and quaternary cyanomethyl pyridinium salts. The reaction is tolerant to substituents of different nature (alkyl, alkoxy, halogen); a limitation is the presence of strong electron-withdrawing substituents in the benzene ring of chromene. During the reaction, the products precipitate and can be isolated by filtration.

引用

页码：1161 / 1166

页数：6

共 32 条

[11] Regio- and diastereoselective synthesis of (E)-3-(2-aminochromen-4-yl)-6-aryl-substituted fulvenes
Koz, Gamze
Sahin, Onur
Coskun, Necdet
[J]. ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2016, 71 (09): : 945 - 951
[12] Enantioselective synthesis of 2-amino-4-(nitromethyl)-4H-chromene-3-carbonitriles from 2-iminochromenes
Koz, Gamze
Koz, Omer
Coskun, Necdet
[J]. SYNTHETIC COMMUNICATIONS, 2016, 46 (10) : 909 - 915
[13] Synthesis of Fe3O4-DOPA-Cu Magnetically Separable Nanocatalyst: A Versatile and Robust Catalyst for an Array of Sustainable Multicomponent Reactions under Microwave Irradiation
Kumari, Mitlesh
Jain, Yachana
Yadav, Priya
Laddha, Harshita
Gupta, Ragini
[J]. CATALYSIS LETTERS, 2019, 149 (08) : 2180 - 2194
[14] Application of novel multi-cationic ionic liquids in microwave assisted 2-amino-4H-chromene synthesis
Kumbhar, Arjun
Jadhav, Sanjay
Shejwal, Rajendra
Rashinkar, Gajanan
Salunkhe, Rajshri
[J]. RSC ADVANCES, 2016, 6 (23) : 19612 - 19619
[15] Li C. -B., 2018, SYNTHESIS-STUTTGART, P3708
[16] Organocatalytic conjugate addition promoted by multi-hydrogen-bond cooperation: access to chiral 2-amino-3-nitrile-chromenes
Li, Wenjun
Huang, Jiayao
Wang, Jian
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (03) : 400 - 406
[17] New HA 14-1 analogues: synthesis of 2-amino-4-cyano-4H-chromenes
Moafi, Leila
Ahadi, Somayeh
Bazgir, Ayoob
[J]. TETRAHEDRON LETTERS, 2010, 51 (48) : 6270 - 6274
[18] Design of New Benzo[h]chromene Derivatives: Antitumor Activities and Structure-Activity Relationships of the 2,3-Positions and Fused Rings at the 2,3-Positions
Okasha, Rawda M.
Alblewi, Fawzia F.
Afifi, Tarek H.
Naqvi, Arshi
Fouda, Ahmed M.
Al-Dies, Al-Anood M.
El-Agrody, Ahmed M.
[J]. MOLECULES, 2017, 22 (03):
[19] Chromenes: potential new chemotherapeutic agents for cancer
Patil, Shivaputra A.
Patil, Renukadevi
Pfeffer, Lawrence M.
Miller, Duane D.
[J]. FUTURE MEDICINAL CHEMISTRY, 2013, 5 (14) : 1647 - 1660
[20] Natural and Synthetic Chromenes, Fused Chromenes, and Versatility of Dihydrobenzo[h]chromenes in Organic Synthesis
Pratap, Ramendra
Ram, Vishnu Ji
[J]. CHEMICAL REVIEWS, 2014, 114 (20) : 10476 - 10526

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