Base-Promoted Multicomponent Reactions: A Synthesis of 2-Amino-1,3-selenazole Derivatives

被引：21

作者：

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

Fang, Yi ^{[1
,2
]}

Wang, Shun-Yi ^{[1
,2
]}

Ji, Shun-Jun ^{[1
,2
]}

机构：

[1] Soochow Univ, Key Lab Organ Synth Jiangsu Prov, Coll Chem Chem Engn & Mat Sci, Suzhou 215123, Peoples R China

[2] Soochow Univ, Collaborat Innovat Ctr Suzhou Nano Sci & Technol, Suzhou 215123, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 05期

基金：

中国国家自然科学基金;

关键词：

ANTIOXIDANT ACTIVITY; ISOCYANIDES; SELENIUM; SELENAZOLES; ACIDS; ORGANOSELENIUM; SELENAZADIENES; INSERTION; AMINES; MIMICS;

D O I：

10.1021/acs.joc.9b03234

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New practical synthesis of 2-amino-1,3-selenazole with transition metal-free multicomponent reaction is reported here. A series of 2-amino-1,3-selenazole derivatives were afforded by the nucleophilic addition of amines to isoselenocyanate formed in situ, followed by Michael addition reaction and aromatization. The products were isolated from moderate to excellent yields.

引用

页码：3508 / 3516

页数：9

共 50 条

[21] Reagent-Controlled Divergent Synthesis of 2-Amino-1,3-Benzoxazines and 2-Amino-1,3-Benzothiazines
Putta, V. P. Rama Kishore
Vodnala, Nagaraju
Gujjarappa, Raghuram
Tyagi, Ujjawal
Garg, Aakriti
Gupta, Sreya
Pujar, Prasad Pralhad
Malakar, Chandi C.
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (02): : 380 - 396
[22] SYNTHESIS AND AUTOXIDATION OF 2-AMINO-1,3-DIALKYLINDOLES
KOST, AN
PORTNOV, YN
GOLUBEVA, GA
POPOVA, AG
MUSHKET, B
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1980, (09): : 1217 - 1221
[23] Base-Promoted Selective Synthesis of 2H-Pyranones and Tetrahydronaphthalenes via Domino Reactions
Thimmarayaperumal, Solaimalai
Shanmugam, Sivakumar
ACS OMEGA, 2017, 2 (08): : 4900 - 4910
[24] Base-promoted tandem synthesis of 2-azaaryl indoline
Chen, Shuguang
Tan, Jiahong
Wu, Hao
Zhao, Quansheng
Shang, Yongjia
ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (46) : 9133 - 9137
[25] Base-Promoted Tandem Synthesis of 2-Azaaryl Tetrahydroquinolines
Chen, Shuguang
Yang, Langxuan
Shang, Yongjia
Mao, Jianyou
Walsh, Patrick J.
ORGANIC LETTERS, 2021, 23 (05) : 1594 - 1599
[26] Aryliodoazide Synthons: A Different Approach for Diversified Synthesis of 2-Aminothiazole, 1,3-Thiazole, and 1,3-Selenazole Scaffolds
Majnooni, Sahar
Duffield, Joseph
Price, Jessica
Khosropour, Ahmad Reza
Zali-Boeini, Hassan
Beyzavi, M. Hassan
ACS COMBINATORIAL SCIENCE, 2019, 21 (07) : 516 - 521
[27] Base-Promoted Tandem Synthesis of 6-H-Phenanthridine and its Derivatives
Jin, Haoyu
Zeng, Min
Wang, Shouliang
Ding, Yitian
Chen, Suyang
Feng, Jinxi
Chen, Xianhao
Miao, Tingting
Wu, Fen
Shi, Qian
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2025, 28 (10)
[28] Electrogenerated base-promoted synthesis of N-benzylic rhodanine and carbamodithioate derivatives
Tissaoui, Khalil
Raouafi, Noureddine
Boujlel, Khaled
JOURNAL OF SULFUR CHEMISTRY, 2010, 31 (01) : 41 - 48
[29] Concise synthesis of N-thiomethyl benzoimidazoles through base-promoted sequential multicomponent assembly
Tian, Jingxin
Yuan, Shanshan
Xiao, Fuhong
Huang, Huawen
Deng, Guo-Jun
RSC ADVANCES, 2019, 9 (52) : 30570 - 30574
[30] Synthesis and BK channel-opening activity of 2-amino-1,3-thiazole derivatives
Qi, Xiao-Lei
Jo, Heeji
Wang, Xue-Ying
Ji, Tong-Tong
Lin, Hai-Xia
Park, Chul-Seung
Cui, Yong-Mei
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2021, 43

← 1 2 3 4 5 →