scholarly journals Copper-catalyzed CuAAC/intramolecular C–H arylation sequence: Synthesis of annulated 1,2,3-triazoles

2012 ◽  
Vol 8 ◽  
pp. 1771-1777 ◽  
Author(s):  
Rajkumar Jeyachandran ◽  
Harish Kumar Potukuchi ◽  
Lutz Ackermann
Keyword(s):  
Catalytic System ◽  
Cascade Reactions ◽  
Direct Access ◽  
One Pot ◽  
Direct Preparation

Step-economical syntheses of annulated 1,2,3-triazoles were accomplished through copper-catalyzed intramolecular direct arylations in sustainable one-pot reactions. Thus, catalyzed cascade reactions involving [3 + 2]-azide–alkyne cycloadditions (CuAAC) and C–H bond functionalizations provided direct access to fully substituted 1,2,3-triazoles with excellent chemo- and regioselectivities. Likewise, the optimized catalytic system proved applicable to the direct preparation of 1,2-diarylated azoles through a one-pot C–H/N–H arylation reaction.

CuSO4–d-glucose, an inexpensive and eco-efficient catalytic system: direct access to diverse quinolines through modified Friedländer approach involving SNAr/reduction/annulation cascade in one pot

RSC Advances ◽  
2015 ◽  
Vol 5 (10) ◽  
pp. 7654-7660 ◽  
Author(s):  
Namrata Anand ◽  
Tanmoy Chanda ◽  
Suvajit Koley ◽  
Sushobhan Chowdhury ◽  
Maya Shankar Singh
Keyword(s):  
Catalytic System ◽  
Direct Access ◽  
One Pot ◽  
Efficient Approach

A one-pot, efficient approach to quinoline synthesis, directly from 2-bromoaromatic aldehydes/ketones in a H2O–EtOH mixture involving a sequence of SNAr/reduction/annulation cascade using CuSO4-d-glucose, is devised.

Physically mixed catalytic system of amino and sulfo-functional porous organic polymers as efficiently synergistic co-catalysts for one-pot cascade reactions

2020 ◽  
Vol 44 (22) ◽  
pp. 9546-9556
Author(s):  
Zunming Sun ◽  
Fuyao Liu ◽  
Xinyue Yang ◽  
Xianpei Huang ◽  
Mengmeng Zhang ◽  
...  
Keyword(s):  
Catalytic System ◽  
Sulfonic Acid ◽  
Polymeric Materials ◽  
Cascade Reactions ◽  
Porous Polymers ◽  
Amino Groups ◽  
Acid Base ◽  
Porous Organic Polymers ◽  
One Pot ◽  
Co Catalysts

Acid/base bi-functional polymeric materials were prepared using physically mixed porous polymers P(DVB-VBS) with sulfonic acid and P(DVB-VBA) with amino groups for various cascade reactions.

An Efficient One-Pot Protocol for Direct Access to Diarylmethyl Thioglycosides with para-Quinone Methides via S-Glycosyl Isothiouronium Salts

Synlett ◽  
2020 ◽  
Vol 31 (17) ◽  
pp. 1713-1719
Author(s):  
Pintu Kumar Mandal ◽  
Atul Dubey
Keyword(s):  
Boron Trifluoride ◽  
Boron Trifluoride Etherate ◽  
Quinone Methide ◽  
Direct Access ◽  
Quinone Methides ◽  
Reaction Conditions ◽  
One Pot ◽  
Direct Preparation ◽  
The One ◽  
Rapid Conversion

An efficient one-pot protocol has been developed for the direct preparation of diarylmethyl thioglycosides starting from per-O-acetylated sugars via glycosyl isothiouronium salts. The one-pot reaction conditions involve rapid conversion of the per-O-acetylated sugar with thiourea in the presence of boron trifluoride etherate as catalyst to give the corresponding glycosyl isothiouronium salt, which is subsequently treated with a para-quinone methide in the presence of a base to give the a diarylmethyl thioglycoside in excellent yield.

Amino- and sulfo-bifunctionalized hyper-crosslinked organic nanotube frameworks as efficient catalysts for one-pot cascade reactions

2019 ◽  
Vol 43 (5) ◽  
pp. 2269-2273 ◽  
Author(s):  
Guojie Meng ◽  
Shengguang Gao ◽  
Ying Liu ◽  
Li Zhang ◽  
Chunmei Song ◽  
...  
Keyword(s):  
Cascade Reactions ◽  
One Pot ◽  
First Time

The synthesis of amino- and sulfo-bifunctionalized hyper-crosslinked organic nanotube frameworks for one-pot cascade reactions was reported for the first time.

Indium-Catalyzed Direct Conversion of Lactones into Thiolactones and Selenolactones in the Presence of Elemental Sulfur and Selenium

Synthesis ◽  
2017 ◽  
Vol 50 (03) ◽  
pp. 565-574 ◽  
Author(s):  
Norio Sakai ◽  
Shuhei Horikawa ◽  
Yohei Ogiwara
Keyword(s):  
Catalytic System ◽  
Elemental Sulfur ◽  
Direct Conversion ◽  
The Novel ◽  
One Pot

The direct conversion of lactones into thiolactones with elemental sulfur (S8) catalyzed by InCl3/PhSiH3 in a one-pot reaction is described. This catalytic system was successfully applied to the novel preparation of selenolactones from lactones and selenium.

scholarly journals Engineering P450 TamI as an Iterative Biocatalyst for Selective Late-Stage C-H Functionalization and Epoxidation of Tirandamycin Antibiotics

2021 ◽  
Author(s):  
Rosa V. Espinoza ◽  
Kersti Caddell Haatveit ◽  
S. Wald Grossman ◽  
Jin Yi Tan ◽  
Caylie A. McGlade ◽  
...  
Keyword(s):  
Natural Product ◽  
Late Stage ◽  
Md Simulations ◽  
Cascade Reactions ◽  
Direct Access ◽  
Tetramic Acid ◽  
Reaction Sequence ◽  
Substrate Reactivity ◽  
Continuous Oxidation

<div> <div> <div> <p>Iterative P450 enzymes are powerful biocatalysts for selective late-stage C-H oxidation of complex natural product scaffolds. These enzymes represent new tools for selectivity and cascade reactions, facilitating direct access to core structure diversification. Recently, we reported the structure of the multifunctional bacterial P450 TamI and elucidated the molecular basis of its substrate binding and strict reaction sequence at distinct carbon atoms of the substrate. Here, we report the design and characterization of a toolbox of TamI biocatalysts, generated by mutations at Leu101, Leu244 and/or Leu295, that alter the native selectivity, step sequence and number of reactions catalyzed, including the engineering of a variant capable of catalyzing a four-step oxidative cascade without the assistance of the flavoprotein and oxidative partner TamL. The tuned enzymes override inherent substrate reactivity enabling catalyst- controlled C-H functionalization and alkene epoxidation of the tetramic acid-containing natural product tirandamycin. Five new, bioactive tirandamycin derivatives (6-10) were generated through TamI-mediated enzymatic synthesis. Quantum mechanics calculations and MD simulations provide important insights on the basis of altered selectivity and underlying biocatalytic mechanisms for enhanced continuous oxidation of the iterative P450 TamI. </p> </div> </div> </div>

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