One-Pot Acid-Catalyzed Ring-Opening/Cyclization/Oxidation of Aziridines with N-Tosylhydrazones: Access to 1,2,4-Triazines

被引：45

作者：

Crespin, Lorene ^{[1
]}

Biancalana, Lorenzo ^{[1
]}

Morack, Tobias ^{[1
]}

Blakemore, David C. ^{[2
]}

Ley, Steven V. ^{[1
]}

机构：

[1] Univ Cambridge, Dept Chem, Lensfield Rd, Cambridge CB2 1EW, England

[2] Pfizer Inc, Med Design, Eastern Point Rd, Groton, CT 06340 USA

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 05期

基金：

英国工程与自然科学研究理事会;

关键词：

DIELS-ALDER REACTION; SUBSTITUTED 1,2,4-TRIAZINES; BENZYLIC ALCOHOLS; DERIVATIVES; LANTHANIDES(III); ACTINIDES(III); ANTIBACTERIAL; ALKYLATION; COMPLEXES; PYRIDINES;

D O I：

10.1021/acs.orglett.7b00101

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new, three-step, telescoped reaction sequence for the regioselective conversion of N-tosyl hydrazones and aziridines to 3,6-disubstituted and 3,5,6-trisubstituted 1,2,4-triazines is described. The process involves an efficient nucleophilic ring opening of the aziridine, giving access to a wide range of aminohydrazones, isolated with excellent yields. A "one-pot" procedure, combining the ring opening with a cyclization and an oxidation step, allows the preparation of diversified triazines in good yields.

引用

页码：1084 / 1087

页数：4

共 43 条

[1]

[Anonymous], [No title captured]

[2] DIELS-ALDER REACTIONS OF HETEROCYCLIC AZADIENES - SCOPE AND APPLICATIONS [J].

BOGER, DL .

CHEMICAL REVIEWS, 1986, 86 (05) :781-793

[3]

Braun R., 2014, PCT Int. Appl., Patent No. [WO 2014053473 A1, 2014053473]

[4] Synthesis of the Louisianin Alkaloid Family via a 1,2,4-Triazine Inverse-Electron-Demand Diels-Alder Approach [J].

Catozzi, Nicola ;

Edwards, Michael G. ;

Raw, Steven A. ;

Wasnaire, Pierre ;

Taylor, Richard J. K. .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (21) :8343-8354

[5] Regioselective Synthesis of V-Shaped Bistriazinyl-phenanthrolines [J].

Coogan, Niall T. ;

Chimes, Michael A. ;

Raftery, James ;

Mocilac, Pavle ;

Denecke, Melissa A. .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (17) :8684-8693

[6] Antibacterial activity of CTBT (7-chlorotetrazolo[5,1-c]benzo[1,2,4]triazine) generating reactive oxygen species [J].

Culakova, Hana ;

Dzugasova, Vladimira ;

Gbelska, Yvetta ;

Subik, Julius .

MICROBIOLOGICAL RESEARCH, 2013, 168 (03) :147-152

[7] Cycloadditions of aryl-substituted 1,2,4-triazines with 2-cyclopropylidene-1,3-dimethylimidazolidine - Zwitterions as discrete intermediates [J].

Ernd, M ;

Heuschmann, M ;

Zipse, H .

HELVETICA CHIMICA ACTA, 2005, 88 (06) :1491-1518

[8] Solvent-free synthesis of triazines using N-halosulfonamides [J].

Ghorbani-Vaghei, Ramin ;

Shahriari, Azadeh ;

Salimi, Zahra ;

Hajinazari, Somayeh .

RSC ADVANCES, 2015, 5 (05) :3665-3669

[9] 1,2,4-Triazine-picolinamide functionalized, nonadentate chelates for the segregation of lanthanides(III) and actinides(III) in biphasic systems [J].

Guillet, Gary L. ;

Hyatt, I. F. Dempsey ;

Hillesheim, Patrick C. ;

Abboud, Khalil A. ;

Scott, Michael J. .

NEW JOURNAL OF CHEMISTRY, 2013, 37 (01) :119-131

[10] Copper-Catalyzed Tandem Nucleophilic Ring-Opening/Intramolecular Oxidative Amidation of N-Tosylaziridines and Hydrazones under Aerobic Conditions [J].

Hong, Deng ;

Lin, Xufeng ;

Zhu, Yuanxun ;

Lei, Ming ;

Wang, Yanguang .

ORGANIC LETTERS, 2009, 11 (24) :5678-5681

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