Access to C4-Functionalized Quinolines via Copper-Catalyzed Tandem Annulation of Alkynyl Imines with Diazo Compounds

Zhu, Ruifeng; Cheng, Guolin; Jia, Chunqi; Xue, Lulu; Cui, Xiuling

doi:10.1021/acs.joc.6b01227

Cited by 41 publications

(8 citation statements)

References 44 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In an intriguing application of copper(I)-catalyzed carbenoids derived from diazoesters 85, Cui and co-workers demonstrated that those can be efficiently trapped by alkynylimines 84 to give rise to allene intermediate 87, which undergoes facile 6π-electrocyclization to form quinolines 86. 36 Wu, Jiang, and co-workers reported and unusual, but nevertheless broadly applicable palladium catalyzed oxidative cyclization of ortho-vinylanilines 88 and alkynes 89 with molecular oxygen, in which ultimately a carbon−carbon bond fission of the stilbene unit occurs. 37 A plausible intermediate in this sequence is 91, which subsequently undergoes carbopalladation to complete the quinoline ring structure.…”

Section: ■ Quinolinesmentioning

confidence: 99%

The Modern Face of Synthetic Heterocyclic Chemistry

2016

View full text Add to dashboard Cite

The synthesis of heterocycles is arguably one of the oldest and at the same time one of the youngest disciplines of organic chemistry. Groundbreaking principles to form heterocycles, mainly by condensation reactions, were recognized in the beginning of the 19th century, and many of the classical reactions discovered at that time are still of great value today. In the 21st century, the wealth of synthetic methodology toward heterocycles is overwhelming, and catalysis, in particular, as one of the cornerstones of green and sustainable chemistry has contributed in a major way to these developments. This perspective tries the impossible by discussing some recent advances in the construction of heterocycles, focusing on catalytic methodology. We are aware that we do not come close to giving adequate credit to the great creativity of chemists in the field.

show abstract

Section: ■ Quinolinesmentioning

confidence: 99%

The Modern Face of Synthetic Heterocyclic Chemistry

2016

View full text Add to dashboard Cite

show abstract

“…In 2006, Cui and co-workers described a copper-catalyzed tandem reaction of alkynyl imines 68 with -diazo esters 20 to provide an efficient method for the synthesis of C4functionalized quinolines 70 (Scheme 21). 27 This reaction involves the in situ formation of allene intermediate 69 followed by 6-electrocyclization and further aromatization to access the target product.…”

Section: Short Review Synthesismentioning

confidence: 99%

Recent Advances in the Tandem Cyclization/Cycloaddition of Allene Intermediates from Copper-Catalyzed Cross-Coupling of Diazo Compounds with Terminal Alkynes

Chen¹,

He²,

Zhou³

et al. 2020

Synthesis

View full text Add to dashboard Cite

This short review summarizes the most recent developments (since 2010) in the tandem cyclization/cycloaddition of allene intermediates, generated from the copper-catalyzed cross-coupling of diazo compounds with terminal alkynes, to afford cyclic compounds.1 Introduction2 Cyclization2.1 Cyclization with Nucleophiles2.2 Cyclization with Electrophiles2.3 6π-Electrocyclization2.4 Other Cyclization3 Cycloaddition4 Conclusion

show abstract

“…[9] We questioned whether this open shell reaction mechanism might be translated to other cascade reaction, thereby delivering a general and efficient route to multisubstituted 4quinolones. As part of our ongoing interest in ynone chemistry, [10] we report herein a base-mediated sequential Michael addition/Smiles rearrangement [11] /N-arylation to generate 1,2,3-trisubstituted 4-quinolones in one step.…”

Section: Introductionmentioning

confidence: 99%

Base‐Promoted Michael Addition/Smiles Rearrangement/ N‐Arylation Cascade: One‐Step Synthesis of 1,2,3‐Trisubstituted 4‐Quinolones from Ynones and Sulfonamides

Liu

et al. 2019

Adv Synth Catal

Self Cite

View full text Add to dashboard Cite

A general, practical, and environmentally friendly protocol to synthesize 1,2,3‐trisubstituted 4‐quinolones from readily available ynones and sulfonamides was developed. The construction of one C−C bond and two C−N bonds via cleavage of one N−S, one C−S, and one C−X (X=F, Cl, Br, O) bond is achieved under transition‐metal‐free conditions in one step. This transformation generates 1 equiv. of sulfur dioxide and 1 equiv. of hydrogen halide as the byproducts. The broad substrate scope and functional group tolerance are demonstrated by 52 examples of 1,2,3‐trisubstituted 4‐quinolones. A preliminary mechanistic study supports a sequential Michael addition/Smiles rearrangement/N‐arylation reaction pathway.

show abstract

Access to C4-Functionalized Quinolines via Copper-Catalyzed Tandem Annulation of Alkynyl Imines with Diazo Compounds

Cited by 41 publications

References 44 publications

The Modern Face of Synthetic Heterocyclic Chemistry

The Modern Face of Synthetic Heterocyclic Chemistry

Recent Advances in the Tandem Cyclization/Cycloaddition of Allene Intermediates from Copper-Catalyzed Cross-Coupling of Diazo Compounds with Terminal Alkynes

Base‐Promoted Michael Addition/Smiles Rearrangement/ N‐Arylation Cascade: One‐Step Synthesis of 1,2,3‐Trisubstituted 4‐Quinolones from Ynones and Sulfonamides

Contact Info

Product

Resources

About