Strategy to Construct 1,2,3-Triazoles by K2CO3-Mediated [4+1] Annulation Reactions of N-Acetyl Hydrazones with Bifunctional Amino Reagents

被引：9

作者：

Zhang, Xiaoke ^{[1
,2
,4
]}

Pan, Yang ^{[1
,4
]}

Wang, Haibo ^{[1
,3
,4
]}

Liang, Chong ^{[1
]}

Ma, Xiaofeng ^{[1
]}

Jiao, Wei ^{[1
]}

Shao, Huawu ^{[1
]}

机构：

[1] Chinese Acad Sci, Nat Prod Res Ctr, Chengdu Inst Biol, Chengdu, Peoples R China

[2] Zunyi Med Univ, Zunyi, Guizhou, Peoples R China

[3] Zhejiang Hongyuan Pharmaceut Co Ltd, Chem & APIs Ind Zone, Taizhou, Zhejiang, Peoples R China

[4] Univ Chinese Acad Sci, Beijing, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2021年 / 363卷 / 02期

基金：

美国国家科学基金会;

关键词：

1,2-diaza-1,3-dienes; N-acetyl hydrazones; annulation; 1,2,3-triazoles; N1; synthon; CATALYTIC ASYMMETRIC-SYNTHESIS; AZIDE-ALKYNE CYCLOADDITION; SITU-GENERATED AZOALKENES; DIELS-ALDER REACTION; DIRECT ACCESS; METAL-FREE; REGIOSELECTIVE SYNTHESIS; TOSYLHYDRAZONES; TRIAZOLES; OLEFINS;

D O I：

10.1002/adsc.202001375

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

K2CO3-mediated [4+1] annulation reactions of N-acetyl hydrazones with bifunctional amino reagents are described, which provide an environmental-friendly strategy to construct 1,2,3-triazoles that does not employ metals, azides, organocatalysis, or oxidants. A series of substituted 1,2,3-triazole derivatives was prepared with good yields.

引用

页码：459 / 463

页数：5

共 50 条

[41] FORMATION OF ORGANOTIN-NITROGEN BONDS .4. N-TRIALKYLTIN DERIVATIVES OF 4-MONO-SUBSTITUTED OR 4,5-DISUBSTITUTED 1,2,3-TRIAZOLES, 3-PHENYL-1,2,4-TRIAZOL, 3-PHENYLPYRAZOLE AND 4-PHENYLIMIDAZOLE
KOZIMA, S
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1972, 44 (01) : 117 - &
[42] REACTIONS OF 1,2-BENZISOTHIAZOL-3-ONE AND 3-THIONE-1, 1-DIOXIDE-N-ACETIC ESTERS WITH HYDRAZINE - UNUSUAL FORMATION OF 4-(SUBSTITUTED AMINO)-1,2,3-BENZOTHIADIAZINE-1,1-DIOXIDES
NABAR, UV
MAYADEO, MS
DEODHAR, KD
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1988, 27 (02): : 109 - 111
[43] SYNTHESIS OF BENZOG QUINOLINE DERIVATIVES .6. ON MECHANISM OF CYCLIZATION REACTION OF BETA-2 CARBOXYNAPHTHYL-3-AMINO PROPIONIC ACID IN N-ACETYL 1,2,3,4-TETRAHYDRO-4-OXOBENZO G QUINOLINE
BEKHLI, AF
KOZYREVA, NP
PERESLEN.EM
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1970, (03): : 394 - +
[44] Novel Cu(0)–Fe3O4@SiO2/NH2cel as an Efficient and Sustainable Magnetic Catalyst for the Synthesis of 1,4-Disubstituted-1,2,3-triazoles and 2-Substituted-Benzothiazoles via One-Pot Strategy in Aqueous Media
Madhvi Bhardwaj
Babita Jamwal
Satya Paul
Catalysis Letters, 2016, 146 : 629 - 644
[45] Novel Cu(0)-Fe3O4@SiO2/NH2cel as an Efficient and Sustainable Magnetic Catalyst for the Synthesis of 1,4-Disubstituted-1,2,3-triazoles and 2-Substituted-Benzothiazoles via One-Pot Strategy in Aqueous Media
Bhardwaj, Madhvi
Jamwal, Babita
Paul, Satya
CATALYSIS LETTERS, 2016, 146 (03) : 629 - 644
[46] V-TRIAZOLO[4,5-D]PYRIMIDINES (8-AZAPURINES) .17. PREPARATION OF 1,6-DIHYDRO-8-AZAPURINES BY HEATING 4-AMINO-5-AMINOMETHYL-N-ALKYL-1,2,3-TRIAZOLES WITH ORTHOESTERS OR AMIDINES
ALBERT, A
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (03): : 291 - 295
[47] OPEN-CHAIN NITROGEN-COMPOUNDS .4. SYNTHESIS OF 5-HYDROXY-1,2,3-TRIAZOLES FROM 1-ARYL-3-(ETHOXYCARBONYLMETHYL)TRIAZENES - A NEW ROUTE TO ALPHA-DIAZO-N-ARYLACETAMIDES
BAINES, KM
VAUGHAN, K
HOOPER, DL
LEVECK, LF
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1983, 61 (07): : 1549 - 1556
[48] Competitive reactivity of the aryl isothiocyanate dipolarophile at N=C versus C=S with nucleophilic 1,3-dipoles:: a combined experimental and theoretical study.: The reactions of substituted 1,2,3-triazolium-1-aminide 1,3-dipoles with aryl isothiocyanates:: new tricyclic thiazolo[4,5-d][1,2,3]triazoles
Butler, RN
Grogan, DC
McDonald, PD
Burke, LA
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (24): : 3587 - 3590
[49] AZAPROPELLANES - NEW FUSED TETRA-AZATRIAZOLO[N.3.3.01,X]-DODECENES AND TRIDECENES - SUBSTITUTED 3,3A,4,5,6,6A-HEXAHYDROPYRROLO[2,3-D]-1,2,3-TRIAZOLES FROM A GENERAL TANDEM CYCLOADDITION-REARRANGEMENT REACTION OF 1,2,3-TRIAZOLIUM IMIDES WITH SUBSTITUTED ALKENES - KINETICS AND MECHANISM - AZOLIUM 1,3-DIPOLES .3.
BUTLER, RN
EVANS, AM
GILLAN, AM
JAMES, JP
MCNEELA, EM
CUNNINGHAM, D
MCARDLE, P
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (09): : 2537 - 2544
[50] Potassium Iodide/tert-Butyl Hydroperoxide-Mediated Oxidative Annulation for the Selective Synthesis of N-Substituted 1,2,3-Benzotriazine-4(3H)-ones Using Nitromethane as the Nitrogen Synthon
Yan, Yizhe
Niu, Bin
Xu, Kun
Yu, Jianhua
Zhi, Huanhuan
Liu, Yanqi
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (02) : 212 - 217

← 1 2 3 4 5 →