An Approach to α- and β-Amino Peroxides via Lewis Acid Catalyzed Ring Opening-Peroxidation of Donor-Acceptor Aziridines and N-Activated Aziridines

被引：8

作者：

Singh, Kuldeep ^{[1
]}

Kumar, Pramod ^{[1
]}

Jagadeesh, Chenna ^{[1
]}

Patel, Manveer ^{[1
]}

Das, Dinabandhu ^{[2
]}

Saha, Jaideep ^{[1
]}

机构：

[1] Ctr Biomed Res CBMR, Div Mol Synth & Drug Discovery, SGPGIMS Campus. Raebareli Rd, Lucknow 226014, Uttar Pradesh, India

[2] Jawaharlal Nehru Univ, Sch Phys Sci, New Delhi, India

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2020年 / 362卷 / 19期

关键词：

Donor-Acceptor aziridine; N-Activated aziridine; Organic Peroxides; N-(alpha-Peroxy) Linkage; ORGANIC PEROXIDES; DRUG-DEVELOPMENT; EFFICIENT; INDOLES; SULFONYLAZIRIDINES; FUNCTIONALIZATION; REARRANGEMENT; CYCLOADDITION; CONSTRUCTION; VERRUCULOGEN;

D O I：

10.1002/adsc.202000815

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Site-selective ring-opening process of two different aziridine classes with hydroperoxide is described herein that provides access to various alpha- and beta-amino and alpha-(imino)-peroxy compounds. This strain-release-driven peroxide addition to aziridines represents an alternative approach for entries to biologically significant heteroatom substituted organic peroxides and complements existing methods in the field. The peroxide products obtained by this method displayed a different reactivity during peroxide-specific rearrangement processes promoted by either acid or base. Mechanistic studies and useful synthetic elaboration of the products have also been presented.

引用

页码：4130 / 4137

页数：8

共 45 条

[1] Lewis Acid Catalyzed SN2-Type Ring Opening of N-Activated Aziridines with Electron-Rich Arenes/Heteroarenes
Ghorai, Manas K.
Tiwari, Deo Prakash
Jain, Nikita
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (14): : 7121 - 7130
[2] Efficient Synthesis of Diarylmethylamines via Lewis Acid Catalyzed Friedel-Crafts Reactions of Donor-Acceptor Aziridines with N,N-Dialkylanilines
Kim, Yerin
Kwon, Yong Il
Kim, Sung-Gon
[J]. SYNTHESIS-STUTTGART, 2020, 52 (02): : 281 - 289
[3] Facile Synthesis of Oxime Amino Ethers via Lewis Acid Catalyzed S N 2-Type Ring Opening of Activated Aziridines with Aryl Aldehyde Oximes
Bhattacharyya, Aditya
Das, Subhomoy
Chauhan, Navya
Biswas, Pronay K.
Ghorai, Manas K.
[J]. SYNLETT, 2020, 31 (07) : 708 - 712
[4] Ring-opening polymerization of donor-acceptor cyclopropanes catalyzed by Lewis acids
Hayakawa, Kosuke
Matsuoka, Shin-ichi
Suzuki, Masato
[J]. POLYMER CHEMISTRY, 2017, 8 (25) : 3841 - 3847
[5] Enantioselective Synthesis of 4,5-Dihydropyrroles via Domino Ring-Opening Cyclization (DROC) of N-Activated Aziridines with Malononitrile
Ghorai, Manas K.
Tiwari, Deo Prakash
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (06): : 2617 - 2625
[6] Synthesis of Chiral Vicinal Amino Alcohol Derivatives via Lewis Acid-Catalyzed Asymmetric Ring Opening of Aziridines with Alcohols and Carboxylic Acids
Ma, Chen-Xue
Hu, Qi
Qin, Hai-Lin
Yang, Gaosheng
Chai, Zhuo
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (07) : 1654 - 1660
[7] Lewis acid-catalyzed [3+3] cycloadditions of donor-acceptor aziridines with N,N-dialkyl-3-vinylanilines via carbon-carbon bond cleavage
Lee, Sang Gyu
Kim, Sung-Gon
[J]. TETRAHEDRON, 2018, 74 (27) : 3671 - 3678
[8] Construction of 3-Substituted Phthalides via Lewis Acid-Catalyzed Intramolecular Ring Opening of Aziridines with Esters
Xing, Siyang
Zhang, Panpan
Tian, Zhen
Yang, Jingmeng
Pang, Yuhao
Liao, Yuanfen
Liu, Yang
Wang, Kui
Zhu, Bolin
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (26)
[9] Nucleophilic Ring Opening of Donor-Acceptor Cyclopropanes Catalyzed by a Bronsted Acid in Hexafluoroisopropanol
Richmond, Edward
Vukovic, Vuk D.
Moran, Joseph
[J]. ORGANIC LETTERS, 2018, 20 (03) : 574 - 577
[10] Lewis Acid Catalyzed Highly Stereoselective Domino-Ring-Opening Cyclization of Activated Aziridines with Enolates: Synthesis of Functionalized Chiral γ-Lactams
Ghorai, Manas K.
Tiwari, Deo Prakash
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (18): : 6173 - 6181

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