Synthesis of 2,5-Disubstituted Oxazoles from Arylacetylenes and α-Amino Acids through an I2/Cu(NO3)2•3H2O-Assisted Domino Sequence

Wang, Jungang; Cheng, Yan; Xiang, Jia‐Chen; Wu, An‐Xin

doi:10.1055/s-0037-1612087

Cited by 6 publications

(1 citation statement)

References 10 publications

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“…5 In addition to this, a variety of synthetic strategies such as cyclization of acyclic compounds, oxidation of oxazolines, coupling of pre-functionalized oxazoles with various organometallic reagents, and other practical methods have been developed for the synthesis of substituted oxazoles. 6 Nonetheless, the exploration of more efficient approaches is of continuous interest, particularly, the development of practical synthetic methodologies towards the synthesis of substituted oxazoles, targeting the distinct activity of advanced starting materials and improving functional group compatibility.…”

Section: Introductionmentioning

confidence: 99%

I₂/TBHP-mediated oxidative cascade cyclization of vinyl azide and benzylamine to construct 2,5-disubstituted oxazoles

Pothireddy¹,

Chatterjee²,

Babu³

et al. 2023

Org. Biomol. Chem.

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Section: Introductionmentioning

confidence: 99%

I₂/TBHP-mediated oxidative cascade cyclization of vinyl azide and benzylamine to construct 2,5-disubstituted oxazoles

Pothireddy¹,

Chatterjee²,

Babu³

et al. 2023

Org. Biomol. Chem.

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Recent Advances for Synthesis of Oxazole Heterocycles via C‐H/C‐N Bond Functionalization of Benzylamines

Kadu

2022

ChemistrySelect

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The five membered heteroaromatic oxazole motifs and their scaffolds exhibit significant pharmaceutical and biological applications. Remarkably, the high efficiency in the assembly of structurally diverse oxazole scaffolds via C(sp 3 )-H functionalization of benzylamines have attracted synthetic organic chemists.In this review, the different synthetic strategies from benzylamines as a new emerging substrate via CÀ H/CÀ N bond functionalization towards oxazole synthesis are discussed in detail. Moreover, it highlights substrate scope along with the reaction mechanism involved during the reaction.

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Acid‐Acid‐Catalyzed Tandem Reactions Driven by an Additive‐Like Component

Chen

Bai

et al. 2020

The Chemical Record

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Acid‐catalyzed tandem reactions with auto‐tandem catalysis are effective for simplifying organic synthesis. However, some of the reported reactions were established based on the use of well‐designed substrate with complex structure. In some cases, owing to the existence of a big gap between each catalytic cycle, it is hard to bind all the individual reaction steps to be a peaceful sequence. To enrich the diversity and also to strengthen the practical usefulness of the methodology developed by auto‐tandem catalysis, an additive‐like component was added to induce acid‐acid‐catalyzed tandem reaction. During the reaction, the additive‐like component acted either as an activator to increase the reactivity of the starting material or a hided reagent to enable successful transformation of the intermediate. Many novel tandem reactions were established in a one‐pot manner with the aid of this strategy. Importantly, this strategy not only allows the use of simple and commercially available chemicals as substrates, but also possesses multiple merits, such as simplifying operation, lowering waste generation and enhancing synthetic efficiency and atom‐economy. A summarization of the additive‐like component‐induced auto‐tandem catalysis with an acid catalyst was given in this review, in which many acid‐acid‐catalyzed tandem reactions were discussed. The reported additive‐like components were classified as three types: oxidative type, reductive type and neutral type depending on their mechanisms in assisting the establishment of acid‐acid‐catalyzed tandem reactions. Many examples were collected and analyzed from the viewpoints of simplifying the synthesis and manifesting their superior and distinct functionalities of the additives. A perspective of this concept was also given at the end of this review.

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Synthesis of 2,5-Disubstituted Oxazoles from Arylacetylenes and α-Amino Acids through an I2/Cu(NO3)2•3H2O-Assisted Domino Sequence

Cited by 6 publications

References 10 publications

I₂/TBHP-mediated oxidative cascade cyclization of vinyl azide and benzylamine to construct 2,5-disubstituted oxazoles

I₂/TBHP-mediated oxidative cascade cyclization of vinyl azide and benzylamine to construct 2,5-disubstituted oxazoles

Recent Advances for Synthesis of Oxazole Heterocycles via C‐H/C‐N Bond Functionalization of Benzylamines

Acid‐Acid‐Catalyzed Tandem Reactions Driven by an Additive‐Like Component

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Synthesis of 2,5-Disubstituted Oxazoles from Arylacetylenes and α-Amino Acids through an I2/Cu(NO3)2•3H2O-Assisted Domino Sequence

Cited by 6 publications

References 10 publications

I2/TBHP-mediated oxidative cascade cyclization of vinyl azide and benzylamine to construct 2,5-disubstituted oxazoles

I2/TBHP-mediated oxidative cascade cyclization of vinyl azide and benzylamine to construct 2,5-disubstituted oxazoles

Recent Advances for Synthesis of Oxazole Heterocycles via C‐H/C‐N Bond Functionalization of Benzylamines

Acid‐Acid‐Catalyzed Tandem Reactions Driven by an Additive‐Like Component

Contact Info

Product

Resources

About

I₂/TBHP-mediated oxidative cascade cyclization of vinyl azide and benzylamine to construct 2,5-disubstituted oxazoles

I₂/TBHP-mediated oxidative cascade cyclization of vinyl azide and benzylamine to construct 2,5-disubstituted oxazoles