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Current Organocatalysis

Author(s): Dnyaneshwar Nighot*, Arvind K. Jain, Imran Ali and Varun Rawat *

DOI: 10.2174/2213337208666211213141836

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One-Pot Access to 2-oxazolines via a Castro-Stephens Coupling and Intramolecular Cyclization

Page: [172 - 178] Pages: 7

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Abstract

Aim: Here, we have reported easy one-pot access to a series of oxazolines using a modified Castro-Stephens coupling protocol.

Background: 2-oxazolines have been shown to have significant biological activity and wide-ranging applications in organic chemistry. These properties make oxazolines as heterocyclic compounds of immense importance.

Objective: The objective of this study is to synthesize oxazoline derivatives via an economical and one-pot protocol.

Methods: 2-oxazoline has been synthesized through Cu-powder mediated Castro-Stephens coupling and intramolecular cyclization route. The mechanism involves a rearrangement in which one of the oxygen from the N-acylamino alcohol group is liberated as water and then transferred to alkyne functionality to form 2-oxazoline derivatives. The oxazolines were characterized by NMR, mass, and XRD studies.

Results: The protocol is economically viable and uses readily available Cu-powder along with DMF for cross-coupling and cyclization steps.

Conclusion: We have reported a one-pot protocol to prepare 2-oxazolines using a Castro-Stephens coupling and intramolecular cyclization.

Keywords: Castro-stephens coupling, cu-powder, cyclization, 5-exo-dig cyclization, heterocyclic compounds, 2-oxazoline.

Graphical Abstract

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