One-Pot Synthesis of 2-Imidazolines via the Ring Expansion of Imidoyl Chlorides with Aziridines

Kuszpit, Michael R.; Wulff, William D.; Tepe, Jetze J.

doi:10.1021/jo200101q

Cited by 29 publications

(10 citation statements)

References 32 publications

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“…In 2011, Kuszpit et al in our lab developed a ring expansion reaction of an aziridine (310) with an imidoyl chloride to synthesize 2-imidazoline (312) (Scheme 87). [86] Initial investigations were done by reacting imidoyl chloride (R 1 = Ph, R 2 = Bn) (313) (Scheme 88) (formed in situ from the reaction of (COCl) 2 and amidine (311)) with aziridine (R 3 = Ph, R 4 = CO 2 Et, R 5 = H) in the presence of different bases (DABCO, DMAP, Et 3 N, ( i Pr) 2 NEt, 2,6-lutidine). The reaction with Hünig's base and Et 3 N was stalled at the intermediate 314 (Scheme 88).…”

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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“…85 The reaction is highly regio-and stereospecific. The imidoyl aziridine 160 is most likely activated by the Bronsted acid, 2,6-lutidine.HCl.…”

Section: Synthesis Of Imidazolinesmentioning

confidence: 99%

Recent applications of aziridine ring expansion reactions in heterocyclic synthesis

Singh¹,

Sudheesh²,

Keroletswe³

2017

Arkivoc

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The inherent reactivity of the aziridine ring due to ring-strain makes it valuable building blocks for the synthesis of other heterocyclic motifs of biological relevance. Of particular significance is the generation of azomethine ylides from them and cycloaddition of ylides with alkenes, alkynes, and heterocumulenes. The ring undergoes opening followed by cyclization with a variety of reagents either in the presence of a catalyst or without any catalyst. This review article discusses the recent applications of aziridines in syntheses of four-to seven-membered heterocycles of biological relevance such as azetidines, 2

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“…For the synthesis and applications of imidoyl chlorides, see: Pelter et al (1975); Manley & Bilodeau (2002); Cunico & Pandey (2005); Raussukana et al (2006); Zheng & Alper (2008); Kuszpit et al (2011). For a related structure of an imidoyl chloride, see: Seidelmann et al (1998).…”

Section: Related Literaturementioning

confidence: 99%

“…(2013). E69, o1384 (Pelter et al, 1975), of highly substituted 2-imidazolines via a ringexpansion reaction with aziridines (Kuszpit et al, 2011), and by in situ reaction with pyridine-1-oxides to give 2-aminopyridine amides (Manley et al, 2002). They have also been used as precursors to α-iminoamides (Cunico et al, 2005), isoquinolin-1(2H)-ones via a palladium-catalyzed reaction with diethyl(2-iodoaryl)malonates (Zheng et al, 2008), and 1,3-oxathiolanones and benzoxathianones by reaction with mercaptocarboxylic acids (Raussukana et al, 2006).…”

Section: Sup-1mentioning

confidence: 99%

(Z)-N-(2,6-Diisopropylphenyl)-4-nitrobenzimidoyl chloride

et al. 2013

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In the title compound, C19H21ClN2O2, the aromatic rings are approximately perpendicular to each other, subtending a dihedral angle of 87.7 (1)°. In the crystal, the 4-nitrophenyl groups of pairs of neighbouring molecules are parallel and oriented head-to-tail with a ring centroid–centroid distance of 3.9247 (12) Å, leading to a π–π interaction between the pair. The faces of each phenyl ring of the 2,6-diisopropylphenyl group interact with two different groups, viz. a chloro group of an adjacent molecule on one side and the edge of the 4-nitrophenyl ring of a second molecule on the other side.

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One-Pot Synthesis of 2-Imidazolines via the Ring Expansion of Imidoyl Chlorides with Aziridines

Abstract: We herein report a simple and convenient one pot synthesis of highly-substituted 2-imidazolines in a regiocontrolled and stereospecific matter through the ring expansion reaction of an imidoyl chloride with an aziridine, analogues to the Heine reaction.

Cited by 29 publications

References 32 publications

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

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

Recent applications of aziridine ring expansion reactions in heterocyclic synthesis

(Z)-N-(2,6-Diisopropylphenyl)-4-nitrobenzimidoyl chloride

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