Microwave‐assisted One‐pot, Three‐component Regiospecific and Sterospecific Synthesis of Spiro Indanone Pyrrolidine/Piperidine Fused Nitrochromene Derivatives Through 1,3‐Dipolar Cycloaddition Reactions

2019 ◽  
Vol 56 (6) ◽  
pp. 1757-1770 ◽  
Author(s):  
Sabita Nayak ◽  
Pravati Panda ◽  
Seetaram Mohapatra ◽  
Bishnuprasad Raiguru ◽  
Nilofar Baral
Keyword(s):  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
One Pot ◽  
Microwave Assisted

Improved Protocols for Microwave-Assisted Cu(I)-Catalyzed Huisgen 1,3-Dipolar Cycloadditions

2007 ◽  
Vol 72 (8) ◽  
pp. 1014-1024 ◽  
Author(s):  
Pedro Cintas ◽  
Katia Martina ◽  
Bruna Robaldo ◽  
Davide Garella ◽  
Luisa Boffa ◽  
...  
Keyword(s):  
Heterogeneous Catalysis ◽  
Microwave Irradiation ◽  
Ultrasound Irradiation ◽  
Conventional Heating ◽  
Dipolar Cycloaddition ◽  
One Pot ◽  
Click Reactions ◽  
Dipolar Cycloadditions ◽  
Microwave Assisted ◽  
New Applications

The Huisgen 1,3-dipolar cycloaddition of azides and acetylenes catalyzed by Cu(I) salts, leading to 1,2,3-triazoles, is one of the most versatile "click reactions". We have developed a series of optimized protocols and new applications of this reaction starting from several substrates, comparing heterogeneous vs homogeneous catalysis, conventional heating vs microwave irradiation or simultaneous microwave/ultrasound irradiation. Both non-conventional techniques strongly promoted the cycloaddition (bromide → azide → triazole), that could be conveniently performed in a one-pot procedure. This was feasible even with such bulky molecules as functionalized β-cyclodextrins (β-CD), starting from 61-O-tosyl-β-CD or from heptakis[6-O-(tert-butyldimethylsilyl)]-21-O-propargyl-β-CD. "Greener" heterogeneous catalysis with charcoal-supported Cu(II) or Cu(I) (prepared under ultrasound) was advantageously employed.

scholarly journals Solvent-free one-pot 1,3-Dipolar cycloaddition reactions of dihydropyran derived nitrone

2012 ◽  
Vol 124 (3) ◽  
pp. 679-685 ◽  
Author(s):  
BHASKAR CHAKRABORTY ◽  
PRAWIN KUMAR SHARMA ◽  
NEELAM RAI ◽  
CHIRAN DEVI SHARMA
Keyword(s):  
Solvent Free ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
One Pot

scholarly journals Design, Microwave-Assisted Synthesis and In Silico Prediction Study of Novel Isoxazole Linked Pyranopyrimidinone Conjugates as New Targets for Searching Potential Anti-SARS-CoV-2 Agents

Molecules ◽  
2021 ◽  
Vol 26 (20) ◽  
pp. 6103
Author(s):  
Faisal K. Algethami ◽  
Maher Cherif ◽  
Salma Jlizi ◽  
Naoufel Ben Ben Hamadi ◽  
Anis Romdhane ◽  
...  
Keyword(s):  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Microwave Assisted Synthesis ◽  
Dimroth Rearrangement ◽  
One Pot ◽  
Microwave Assisted ◽  
Three Component Reaction ◽  
Key Steps ◽  
Modes Of Interaction ◽  
Native Ligand

A series of novel naphthopyrano[2,3-d]pyrimidin-11(12H)-one containing isoxazole nucleus 4 was synthesized under microwave irradiation and classical conditions in moderate to excellent yields upon 1,3-dipolar cycloaddition reaction using various arylnitrile oxides under copper(I) catalyst. A one-pot, three-component reaction, N-propargylation and Dimroth rearrangement were used as the key steps for the preparation of the dipolarophiles3. The structures of the synthesized compounds were established by 1H NMR, 13C NMR and HRMS-ES means. The present study aims to also predict the theoretical assembly of the COVID-19 protease (SARS-CoV-2 Mpro) and to discover in advance whether this protein can be targeted by the compounds 4a–1 and thus be synthesized. The docking scores of these compounds were compared to those of the co-crystallized native ligand inhibitor (N3) which was used as a reference standard. The results showed that all the synthesized compounds (4a–l) gave interesting binding scores compared to those of N3 inhibitor. It was found that compounds 4a, 4e and 4i achieved greatly similar binding scores and modes of interaction than N3, indicating promising affinity towards SARS-CoV-2 Mpro. On the other hand, the derivatives 4k, 4h and 4j showed binding energy scores (−8.9, −8.5 and −8.4 kcal/mol, respectively) higher than the Mpro N3 inhibitor (−7.0 kcal/mol), revealing, in their turn, a strong interaction with the target protease, although their interactions were not entirely comparable to that of the reference N3.

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