scholarly journals An efficient and facile access to highly functionalized pyrrole derivatives

2018 ◽  
Vol 14 ◽  
pp. 884-890 ◽  
Author(s):  
Meng Gao ◽  
Wenting Zhao ◽  
Hongyi Zhao ◽  
Ziyun Lin ◽  
Dongfeng Zhang ◽  
...  
Keyword(s):  
Medicinal Chemistry ◽  
Alcohol Solution ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Complete Oxidation ◽  
One Pot ◽  
Pyrrole Derivatives ◽  
Chemistry Research ◽  
Efficient Construction ◽  
Sodium Alkoxide

A straightforward and one-pot synthesis of pyrrolo[3,4-c]pyrrole-1,3-diones via Ag(I)-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with N-alkyl maleimide, followed by readily complete oxidation with DDQ, has been successfully developed. Further transformation with alkylamine/sodium alkoxide alcohol solution conveniently afforded novel polysubstituted pyrroles in good to excellent yields. This methodology for highly functionalized pyrroles performed well over a broad scope of substrates. It is conceivable that this efficient construction method for privileged pyrrole scaffolds could deliver more active compounds for medicinal chemistry research.

A Revised Modular Approach to D8-THC and Derivatives Through Late-Stage Suzuki-Miyaura Cross-Coupling Reactions

2019 ◽  
Author(s):  
Victor Bloemendal ◽  
Floris P. J. T. Rutjes ◽  
Thomas J. Boltje ◽  
Daan Sondag ◽  
Hidde Elferink ◽  
...  
Keyword(s):  
Biological Activity ◽  
Late Stage ◽  
Medicinal Chemistry ◽  
Cross Coupling ◽  
Modular Approach ◽  
Coupling Reactions ◽  
One Pot ◽  
Biologically Relevant ◽  
Cross Coupling Reactions ◽  
Chemistry Research

<p>In this manuscript we describe a modular pathway to synthesize biologically relevant (–)-<i>trans</i>-Δ<sup>8</sup>-THC derivatives, which can be used to modulate the pharmacologically important CB<sub>1</sub> and CB<sub>2</sub> receptors. This pathway involves a one-pot Friedel-Crafts alkylation/cyclization protocol, followed by Suzuki-Miyaura cross-coupling reactions and gives rise to a series of new Δ<sup>8</sup>-THC derivatives. In addition, we demonstrate using extensive NMR evidence that similar halide-substituted Friedel-Crafts alkylation/cyclization products in previous articles were wrongly assigned as the para-isomers, which also has consequence for the assignment of the subsequent cross-coupled products and interpretation of their biological activity. </p> <p>Considering the importance of the availability of THC derivatives in medicinal chemistry research and the fact that previously synthesized compounds were wrongly assigned, we feel this research is describing a straightforward pathway into new cannabinoids.</p>

Concise Synthesis of Tryptanthrin Spiro Analogues with In Vitro Antitumor Activity Based on One-Pot, Three-Component 1,3-Dipolar Cycloaddition of Azomethine Ylides to Сyclopropenes

Synthesis ◽  
2018 ◽  
Vol 51 (03) ◽  
pp. 713-729 ◽  
Author(s):  
Vitali Boitsov ◽  
Alexander Stepakov ◽  
Alexander Filatov ◽  
Nickolay Knyazev ◽  
Stanislav Shmakov ◽  
...  
Keyword(s):  
Antitumor Activity ◽  
Azomethine Ylides ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
One Pot ◽  
Economic Method ◽  
Reaction Proceeds ◽  
High Yields

A simple, efficient and atom-economic method has been developed for the synthesis of complex alkaloid-like compounds with spiro-fused indolo[2,1-b]quinazoline and cyclopropa[a]pyrrolizine or 3-azabicyclo[3.1.0]hexane moieties. We have found that one-pot, three-component 1,3-dipolar cycloaddition reactions allow the desired products to be obtained from various cyclopropene derivatives with tryptanthrin-derived azomethine ylides generated in situ, in good to high yields and excellent diastereoselectivity. The possibility of ylide generation was exemplified by using α-amino acids (l-proline, l-4-thiazolidincarboxylic acid) and simplest peptides (dipeptide Gly-Gly, tripeptide Gly-Gly-Gly). Quantum chemical investigations indicate that the reaction proceeds through the S-shaped azomethine ylide, the interaction of which with cyclopropenes proceeds via a less sterically hindered endo-transition state. The antitumor activity of some of spiro-tryptanthrin derivatives against erythroleukemia (K562), cervical carcinoma (HeLa) and colon carcinoma (CT26) cell lines was evaluated in vitro by MTS-assay.

A highly diastereoselective one-pot three-component 1,3-dipolar cycloaddition of cyclopropenes with azomethine ylides generated from 11H-indeno[1,2-b]-quinoxalin-11-ones

2018 ◽  
Vol 5 (4) ◽  
pp. 595-605 ◽  
Author(s):  
A. S. Filatov ◽  
N. A. Knyazev ◽  
M. N. Ryazantsev ◽  
V. V. Suslonov ◽  
A. G. Larina ◽  
...  
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Efficient Synthesis ◽  
One Pot

A simple and efficient synthesis of compounds with spiro-fused 11H-indeno[1,2-b]quinoxaline and azabicyclo[3.1.0]hexane or cyclopropa[a]pyrrolizine moieties was developed.

Decarboxylative, diastereoselective and exo-selective 1,3-dipolar cycloaddition for diversity-oriented construction of structurally spiro-[butyrolactone-pyrrolidine-chromanone] hybrids

Synlett ◽  
2021 ◽  
Author(s):  
Dong-Gui Guo ◽  
Zheng Li ◽  
Xiao-Xue Han ◽  
Lei Zhang ◽  
Min Zhang ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Transition State ◽  
Medicinal Chemistry ◽  
Homoserine Lactone ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Mild Conditions ◽  
Good Substrate ◽  
Substrate Tolerance

Inspired by the chemistry and biology of butyrolactones, pyrrolidines and chromanones, herein we successfully developed a simple domino 1,3-dipolar cycloaddition of homoserine lactone-derived azomethine ylides for construction of biologically important spiro-[butyrolactone-pyrrolidine-chromanone] hybrids in the presence of the catalyst Et3N under mild conditions. It is based on the application of carboxylic acid activated chromones as dienophiles followed by a decarboxylation process. This reaction displayed good substrate tolerance and gave the desired products in moderate to good yields with high diastereoselectivities via an exo-transition state (up to 85% yield and >20:1 diastereomeric ratio). In particular, this is the first example of introduction of chromanone moiety into spiro [butyrolactone-pyrrolidine] frameworks, which might be valuable in medicinal chemistry.

Diastereoselective synthesis of indolenine-based spiro[pyrazolone-4,2’-pyrrolidine] scaffolds via 1,3-dipolar cycloaddition of 4-aminopyrazolones, aldehydes, and indolenines

2021 ◽  
Author(s):  
Baomin Wang ◽  
Shah Nawaz ◽  
Shiqiang Wei ◽  
Yue Huang ◽  
Wenyao Wang ◽  
...  
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Diastereoselective Synthesis ◽  
One Pot

In this work, we report a novel one-pot [3+2] cycloaddition of 4-aminopyrazolones, indolenines, and aldehydes. The reaction utilized the in-situ generated azomethine ylides as 1,3-dipoles and 2-alkenylindolenines as dipolarophiles affording...

A One-Pot Synthesis of Highly Functionalized Indolizines by 1,3-Dipolar Cycloaddition of Azomethine Ylides and Phosphorylated Hydroxyketenimines

Synlett ◽  
2016 ◽  
Vol 27 (18) ◽  
pp. 2601-2605 ◽  
Author(s):  
Issa Yavari ◽  
Maryam Naeimabadi ◽  
Reza Hosseinpour ◽  
Mohammad Halvagar
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
One Pot ◽  
One Pot Synthesis
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