Thermal Rearrangement of Azido Ketones into Oxazoles via Azirines: One‐Pot, Metal‐Free Heteroannulation to Functionalized 1,3‐Oxazoles

Shah, Shailesh R.; Navathe, Sudhanva S.; Dikundwar, Amol G.; Row, Tayur N. Guru; Vasella, Andrea

doi:10.1002/ejoc.201201269

Cited by 16 publications

(7 citation statements)

References 47 publications

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“…. In recent years, many strategies have been developed on the synthesis of oxazole compounds, such as condensations, cyclizations, transition-metal-catalyzed addition of diazo compounds to nitriles, and rearrangements . Despite the exciting achievements on the synthesis of oxazole derivatives, the exploration of expedient and novel methods for the construction of oxazole derivatives is still commercioganic.…”

mentioning

confidence: 99%

Gold-Catalyzed Radical-Involved Intramolecular Cyclization of Internal N-Propargylamides for the Construction of 5-Oxazole Ketones

Mai

Xuan

et al. 2018

J. Org. Chem.

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An expedient strategy for the synthesis of 5-oxazole ketones was developed via homogeneous gold catalysis with 4-MeO-TEMPO as an oxidant. The desired 5-oxazole ketones were achieved in decent yields with an excellent functional group compatibility under mild conditions. The current protocol also represents the first example for merging a gold catalyst and radical chemistry in one-pot synthesis with internal N-propargylamides.

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confidence: 99%

Gold-Catalyzed Radical-Involved Intramolecular Cyclization of Internal N-Propargylamides for the Construction of 5-Oxazole Ketones

Mai

Xuan

et al. 2018

J. Org. Chem.

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“…Shah et al reported another similar type of microwave‐assisted 2 H ‐aziridine formation reaction. Thermal rearrangement of α‐azidoacetophenone into alkenyl azide, 2‐aryl‐1,3‐oxazole‐4‐carbaldehyde is produced by rearrangement of the carbon skeleton when exposed to DMF‐POCl 3 (Scheme 57) [77].…”

Section: Decomposition Of Vinyl Azidesmentioning

confidence: 99%

Synthesis of various functionalized 2H‐azirines: An updated library

Majee

2021

Journal of Heterocyclic Chem

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In the current extensive review, we pay special attention to the progress in the synthesis of 2H‐azirine. Content is organized by several main approaches for the synthesis of 2H‐azirines such as‐ Neber rearrangement, decomposition of vinyl azides, oxidative cyclization of enamines, ring contraction of isoxazoles or oxazaphospholes, radical addition/cyclization of alkynes, Swern oxidation or elimination reactions of aziridine derivatives, catalytic decomposition of α‐oximino diazo compounds, addition of silyldibromomethyllithium compounds to nitriles, addition of carbenes to nitriles and via azirine‐azirine transformations. Some of these approaches open up access to new 2H‐azirine derivatives and make the already established compounds more convenient. A description of these methods and the progress of using well‐known reactions leading to the aziridine system are presented in this section. This review surveys the progress of various functionalized 2H‐azirine formation reactions from the exploration period to the present.

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“…Representative flexi-arm tripodal host molecules 6a,c In continuation of our interest in C 3 -symmetric compounds 12 in biologically potent compounds 13 and in oxazole chemistry, 14 we report herein the synthesis and study of flexible tripodal 1,3-oxazoles by employing 1,3,5-trimethylbenzene as the substrate for transformation into C 3 -symmetric scaffolds.…”

Section: Figurementioning

confidence: 99%

Conformationally Flexible C 3-Symmetric 1,3-Oxazoles as Molecular Scaffolds

Shah

Thakore

Vyas

et al. 2015

Synlett

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Flexible-arm, C 3 -symmetric tris-oxazoles are synthesized for their applications in supramolecular chemistry and materials science. The C 3 -symmetry is introduced starting from 1,3,5-trimethylbenzene and carrying out threefold reactions at each stage of the synthesis. The applicability of these tris-oxazoles is demonstrated by transforming a representative example into a highly fluorescent material. This is accomplished by conjugation with an aromatic moiety via palladium(0)catalyzed direct arylation at C-2 of the oxazole. A unique molecular arrangement in the crystal structure is observed.

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Thermal Rearrangement of Azido Ketones into Oxazoles via Azirines: One‐Pot, Metal‐Free Heteroannulation to Functionalized 1,3‐Oxazoles

Cited by 16 publications

References 47 publications

Gold-Catalyzed Radical-Involved Intramolecular Cyclization of Internal N-Propargylamides for the Construction of 5-Oxazole Ketones

Gold-Catalyzed Radical-Involved Intramolecular Cyclization of Internal N-Propargylamides for the Construction of 5-Oxazole Ketones

Synthesis of various functionalized 2H‐azirines: An updated library

Conformationally Flexible C 3-Symmetric 1,3-Oxazoles as Molecular Scaffolds

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