A New and Efficient Procedure for Bi(OTf)<sub>3</sub>‐Promoted [3+2] Cycloaddition of <i>N</i>‐Tosylaziridines to Yield Imidazolines

Li, Xing; Yang, Xueqi; Chang, Hong; Li, Yanwei; Ni, Bin; Wei, Wuran

doi:10.1002/ejoc.201100270

Cited by 32 publications

(8 citation statements)

References 46 publications

(10 reference statements)

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“…Li et al reported a Lewis acid-mediated [3 + 2]cycloaddition reaction of N-tosylaziridines (315) with nitriles (316) to synthesize 2-imidazolines (317) (Scheme 89). [87] After the initial Lewis acid screening, Bi(OTf) 3 was found to be a suitable reagent to execute the synthesis. With different aromatic-substituted (R 1 = aryl) aziridines (315), the imidazolines were isolated in good to excellent yields (up to 99%).…”

Section: Methods E: Synthesis Of Imidazolines From Aziridinesmentioning

confidence: 99%

Recent Advances in the Synthesis of Imidazolines (2009–2020)

Mehedi

Tepe

2020

Adv Synth Catal

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Imidazoline is an important class of compounds found in numerous natural and pharmaceutical products. The compounds are also used as an intermediate in the synthesis of organic molecules. Moreover, chiral imidazolines are widely utilized as organocatalysts to synthesize various natural and synthetic organic compounds. In the past decade, there was an increase in interest in developing new methods to synthesize these imidazoline analogs. Both modification of the previously established methods and the development of new methods are carried out significantly. This review article highlights the progress of the synthesis of imidazoline scaffolds in the last few years (2009-present). The review also described the proposed mechanism illustrated in many of the reports.

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Section: Methods E: Synthesis Of Imidazolines From Aziridinesmentioning

confidence: 99%

Recent Advances in the Synthesis of Imidazolines (2009–2020)

Mehedi

Tepe

2020

Adv Synth Catal

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“…Formal [119,120], Sc(OTf) 3 [121], Bi(OTf) 3 [122], etc., have been utilized for this transformation. Recently, a regioselective synthesis of 4-(trifluoromethyl)-1,3- …”

Section: Synthesis Of Imidazolidines Imidazolines and Imidazolesmentioning

confidence: 99%

Ring Expansions of Activated Aziridines and Azetidines

Ghorai

Bhattacharyya

Das

et al. 2015

Topics in Heterocyclic Chemistry

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Facile construction of small and normal-sized, or more precisely, four to seven-membered aza-heterocyclic ring systems is always a challenging yet rewarding task for the synthetic organic chemists. Fortunately, activated aziridines and azetidines provide a direct and convenient access to this coveted molecular architectures through several elegant ring-expansion approaches. This chapter presents some of the illustrative and contemporary examples to demonstrate the synthetic diversity and efficiency of the ring-expansion strategies of activated aziridines and azetidines towards a vast array of small to normal-sized aza-heterocyclic moieties.

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“…A Bi(OTf) 3 ‐mediated direct synthesis of imidazolines starting from aliphatic or aromatic nitriles and N ‐tosylaziridines was developed . An extensive screening of reaction conditions indicated that the reactions could be performed, but with lower yields, with other Lewis acids such as ZnCl 2 , Sm(OTf) 3 , In(OTf) 3 or ZrCl 4 .…”

Section: Activation Of Nitrogen‐containing Functionsmentioning

confidence: 99%

Cyclisations Catalysed by Bismuth(III) Triflate

2016

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Cyclisation reactions have always drawn the attention of organic chemists in pursuit of methods for the selective construction of natural‐product‐like polycyclic compounds. The search for new and efficient ring‐forming reactions has witnessed growing interest, resulting in the design of many elegant synthetic strategies and the discovery of useful methodologies. In this context, cycloisomerisation reactions are very attractive, because they allow for the rapid generation of molecular complexity with use of a low loading of a promoter, thus limiting waste production. The search for sustainable and more efficient catalytic systems remains challenging. Relatively nontoxic and inexpensive bismuth(III) salts are of particular interest for catalytic organic synthesis. More specifically, the highly active triflate salt is known to be noncorrosive and easy to handle. This microreview focuses on cyclisation reactions assisted by bismuth(III) triflate catalysis.

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A New and Efficient Procedure for Bi(OTf)₃‐Promoted [3+2] Cycloaddition of N‐Tosylaziridines to Yield Imidazolines

Cited by 32 publications

References 46 publications

Recent Advances in the Synthesis of Imidazolines (2009–2020)

Recent Advances in the Synthesis of Imidazolines (2009–2020)

Ring Expansions of Activated Aziridines and Azetidines

Cyclisations Catalysed by Bismuth(III) Triflate

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A New and Efficient Procedure for Bi(OTf)3‐Promoted [3+2] Cycloaddition of N‐Tosylaziridines to Yield Imidazolines

Cited by 32 publications

References 46 publications

Recent Advances in the Synthesis of Imidazolines (2009–2020)

Recent Advances in the Synthesis of Imidazolines (2009–2020)

Ring Expansions of Activated Aziridines and Azetidines

Cyclisations Catalysed by Bismuth(III) Triflate

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A New and Efficient Procedure for Bi(OTf)₃‐Promoted [3+2] Cycloaddition of N‐Tosylaziridines to Yield Imidazolines