Synthesis of fused imidazo azepine derivatives by sequential van Leusen/enyne metathesis reactions

Gracias, Vijaya; Gasiecki, Alan F.; Djurić, Stevan W.

doi:10.1016/j.tetlet.2005.10.089

Cited by 40 publications

(11 citation statements)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Ruthenium-catalyzed RCM of 1,7-, 1,8-, and 1,9-enynes were described [1257][1258][1259][1260]. A mechanism involving an ene-thenyne metathesis of tethered enynes was supported by labeling experiments [1261].…”

Section: Metathesis Reactionsmentioning

confidence: 99%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

View full text Add to dashboard Cite

Section: Metathesis Reactionsmentioning

confidence: 99%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

View full text Add to dashboard Cite

“…The condensation reaction of 4-pentenal 34 with but-2-yn-1-amine 38 in DMF at room temperature gives the imine in situ, and then adds phenyl TosMIC 18 and K2CO3 to access the van Leusen imidazole product 39 in high yield. Subsequent cyclization via the intramolecular enyne metathesis reaction results in the formation of the cyclized product 40 containing the diene functional group and their derivatives (Scheme 9, bottom) [35]. Initially, they reported a new protocol employing the van Leusen three-component reaction and the ring-closing metathetical reaction in a sequence method, to form a fused bicyclic imidazole ring.…”

Section: Developments Of the Van Leusen Imidazole Synthesismentioning

confidence: 99%

Synthesis of Imidazole-Based Medicinal Molecules Utilizing the van Leusen Imidazole Synthesis

Zheng

Zhang

2020

Pharmaceuticals

View full text Add to dashboard Cite

Imidazole and its derivatives are one of the most vital and universal heterocycles in medicinal chemistry. Owing to their special structural features, these compounds exhibit a widespread spectrum of significant pharmacological or biological activities, and are widely researched and applied by pharmaceutical companies for drug discovery. The van Leusen reaction based on tosylmethylisocyanides (TosMICs) is one of the most appropriate strategies to synthetize imidazole-based medicinal molecules, which has been increasingly developed on account of its advantages. In this review, we summarize the recent developments of the chemical synthesis and bioactivity of imidazole-containing medicinal small molecules, utilizing the van Leusen imidazole synthesis from 1977.

show abstract

“…31 Gracias reported on the synthesis of 5/6-, 5/7-and 5/8-fused imidazo azepine derivatives by RCEYM reactions (Scheme 13). 32 The starting imidazoles, such as compound 67, were prepared from tosylmethyl isocyanides, primary amines and aldehydes or from secondary amino aldehydes and amino esters by the van Leusen reaction. Noteworthy is that for the enyne ring closure it was necessary to pretreat the imidazoles with an equivalent of p-TsOH to form the corresponding imidazolium ions.…”

Section: Examples Of Heterocycle Syntheses By Rceymmentioning

confidence: 99%

Ring closing enyne metathesis: A powerful tool for the synthesis of heterocycles

2007

View full text Add to dashboard Cite

The ring closing metathesis (RCM) is a powerful method in organic synthesis for the preparation of cyclic compounds by formation of new carbon-carbon bonds. In the past years a particular subclass of the RCM, the ring closing enyne metathesis (RCEYM), has attracted attention due to its synthetic potential in the generation of ring structures with 1,3-diene moieties, which can subsequently be further functionalised. In this tutorial review mechanistic considerations will be described and the synthetic power of this useful and attractive carbon-carbon bond forming reaction will be illustrated by recent examples of RCEYM applications in the preparation of heterocyclic compounds.

show abstract

Synthesis of fused imidazo azepine derivatives by sequential van Leusen/enyne metathesis reactions

Cited by 40 publications

References 42 publications

Transition metals in organic synthesis: Highlights for the year 2005

Transition metals in organic synthesis: Highlights for the year 2005

Synthesis of Imidazole-Based Medicinal Molecules Utilizing the van Leusen Imidazole Synthesis

Ring closing enyne metathesis: A powerful tool for the synthesis of heterocycles

Contact Info

Product

Resources

About