I2/TBHP mediated diastereoselective synthesis of spiroaziridines

被引：20

作者：

Ashitha, Kizhakkan Thiruthi ^{[1
,2
]}

Vinaya, Puthiya Purayil ^{[1
]}

Krishna, Ajay ^{[1
]}

Vincent, Deepthy Cheeran ^{[1
]}

Jalaja, Renjitha ^{[1
,2
]}

Varughese, Sunil ^{[1
]}

Somappa, Sasidhar Balappa ^{[1
,2
]}

机构：

[1] NIIST, CSIR, Chem Sci & Technol Div, Organ Chem Sect, Thiruvananthapuram 695019, Kerala, India

[2] Acad Sci & Innovat Res AcSIR, New Delhi 110001, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2020年 / 18卷 / 08期

关键词：

AZIRIDINES; 3-YLIDENEOXINDOLES; REACTIVITY; IODINE;

D O I：

10.1039/c9ob02711d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Eventhough spiroheterocycles are considered as emerging drug candidates, synthesis of spiroaziridines has not been well explored so far. Herein, we disclose an efficient I-2/TBHP mediated diastereoselective synthesis of N-alkyl spiroaziridines from primary amines and easily accessible alpha,beta-unsaturated ketones. The reaction is also compatible for the synthesis of 2-aroylaziridines.

引用

页码：1588 / 1593

页数：6

共 34 条

[1] Synthesis of Functionalized Spiroaziridine-oxindoles from 3-Ylideneoxindoles: An Easy Route to 3-(Aminoalkyl)oxindoles [J].

Ammetto, I. ;

Gasperi, T. ;

Loreto, M. Antonietta ;

Migliorini, A. ;

Palmarelli, F. ;

Tardella, P. Antonio .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (35) :6189-6197

[2] BF3•OEt2-Mediated Tandem Annulation: A Strategy To Construct Functionalized Chromeno- and Pyrano-Fused Pyridines [J].

Ashitha, K. T. ;

Kumar, V. Praveen ;

Salfeena, C. T. Fathimath ;

Sasidhar, B. S. .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (01) :113-124

[3] FR900482 class of anti-tumor drugs cross-links oncoprotein HMG I/Y to DNA in vivo [J].

Beckerbauer, L ;

Tepe, JJ ;

Cullison, J ;

Reeves, R ;

Williams, RM .

CHEMISTRY & BIOLOGY, 2000, 7 (10) :805-812

[4] Synthesis and Reactivity of 2-(Carboxymethyl)aziridine Derivatives [J].

Callebaut, Gert ;

Meiresonne, Tamara ;

De Kimpe, Norbert ;

Mangelinckx, Sven .

CHEMICAL REVIEWS, 2014, 114 (16) :7954-8015

[5]

Chen H.-J.J., 2016, International Patent No. W02016182938A1, Patent No. [W02016182938A1, 2016182938]

[6] Recent Advances in the Stereoselective Synthesis of Aziridines [J].

Degennaro, Leonardo ;

Trinchera, Piera ;

Luisi, Renzo .

CHEMICAL REVIEWS, 2014, 114 (16) :7881-7929

[7] Recent progress in asymmetric synthesis of aziridine derivatives (microreview) [J].

Dogan, Ozdemir ;

Polat-Cakir, Sidika .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2018, 54 (04) :397-399

[8] Iodine in Modern Oxidation Catalysis [J].

Finkbeiner, Peter ;

Nachtsheim, Boris J. .

SYNTHESIS-STUTTGART, 2013, 45 (08) :979-999

[9] Iodine-Catalyzed C-N Bond Formation: Synthesis of 3-Aminoquinoxalinones under Ambient Conditions [J].

Gupta, Abhishek ;

Deshmukh, Mahesh Subhashrao ;

Jain, Nidhi .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (09) :4784-4792

[10] Ficellomycin: an aziridine alkaloid antibiotic with potential therapeutic capacity [J].

He, Xihong ;

Li, Meng ;

Song, Shuting ;

Wu, Xiaonong ;

Zhang, Jing ;

Wu, Guoguo ;

Yue, Rong ;

Cui, Huanhuan ;

Song, Siqing ;

Ma, Congcong ;

Lu, Fuping ;

Zhang, Huitu .

APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 2018, 102 (10) :4345-4354

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