A Mini-Review: Achievements in the Thiolysis of Epoxides

2020 ◽  
Vol 17 (4) ◽  
pp. 352-362 ◽  
Author(s):  
Zhihua Chen ◽  
Saeed Mohammadi Nasr ◽  
Mosstafa Kazemi ◽  
Masoud Mohammadi
Keyword(s):  
Natural Products ◽  
Bioactive Compounds ◽  
Ring Opening ◽  
Solvent Free ◽  
Organosulfur Compounds ◽  
Important Class ◽  
Research Groups ◽  
Diverse Range ◽  
Solvent Free Conditions ◽  
Ring Opening Reactions

The β-hydroxy sulfides are an important class of organosulfur compounds that have a key role in the synthesis of bioactive compounds containing biological and natural products. The thiolysis of epoxides is the most common and best route for the synthesis of β-hydroxy sulfides. During the last decade, the applications of a diverse range of catalysts and promoter agents in green and organic mediums as well as under solvent-free conditions for the regioselective ring-opening reactions of epoxides with thiols in order to synthesize β-hydroxy sulfides have been studied by various research groups. This review is focused on the important achievements reported in the literature for the thiolysis of epoxides.

Enantioselective Vinylogous Reactions of 3-Alkylidene Oxindoles

Synthesis ◽  
2018 ◽  
Vol 50 (13) ◽  
pp. 2463-2472 ◽  
Author(s):  
Renato Dalpozzo ◽  
Raffaella Mancuso
Keyword(s):  
Natural Products ◽  
Asymmetric Synthesis ◽  
Bioactive Compounds ◽  
Carbonyl Compounds ◽  
Important Class ◽  
Chiral Molecules ◽  
Research Groups ◽  
Mannich Reactions ◽  
The Creation ◽  
Synthetic Derivatives

Oxindoles represent an important class of bioactive compounds and synthetic derivatives found in many natural products. Most of these compounds are chiral molecules and the challenge of their asymmetric synthesis has fascinated many research groups. In particular, the creation of chiral centers out of the oxindole ring by vinylogous addition to 3-alkylidene-substituted oxindoles (3-alkylidene-1,3-dihydro-2H-indol-2-ones) has emerged in recent years. This review aims to give an overview of this topic.1 Introduction2 Aldol and Mannich Reactions3 Addition to Unsaturated Carbonyl Compounds4 Addition to Nitroalkenes5 Miscellaneous6 Conclusion

Solid lithium perchlorate as a powerful catalyst for the synthesis of β-aminoalcohols under solvent-free conditions

2005 ◽  
Vol 83 (5) ◽  
pp. 505-507 ◽  
Author(s):  
Najmodin Azizi ◽  
Mohammad R Saidi
Keyword(s):  
Ring Opening ◽  
Room Temperature ◽  
Lithium Perchlorate ◽  
Solvent Free ◽  
Solvent Free Conditions ◽  
Reaction Proceeds ◽  
Ring Opening Of Epoxides ◽  
Neutral Conditions ◽  
Hindered Amines ◽  
Short Times

Lithium perchlorate catalyzed the ring opening of epoxides with amines to provide the corresponding β-aminoalcohols in excellent yields with high regioselectivity. The reaction proceeds rapidly under mild and neutral conditions and worked well with primary, secondary, aliphatic, aromatic, and hindered amines in short times at room temperature, in the absence of solvent.Key words: epoxide, lithium perchlorate, β-aminoalcohols, solvent-free.

scholarly journals Epoxide Syntheses and Ring-Opening Reactions in Drug Development

Catalysts ◽  
2020 ◽  
Vol 10 (10) ◽  
pp. 1117
Author(s):  
Fotini Moschona ◽  
Ioanna Savvopoulou ◽  
Maria Tsitopoulou ◽  
Despoina Tataraki ◽  
Gerasimos Rassias
Keyword(s):  
Ring Opening ◽  
Large Scale ◽  
Phase Transfer ◽  
Hiv Protease ◽  
Main Stream ◽  
Hiv Protease Inhibitors ◽  
Chiral Phase ◽  
Diverse Range ◽  
Ring Opening Reactions ◽  
Catalytic Asymmetric

This review concentrates on success stories from the synthesis of approved medicines and drug candidates using epoxide chemistry in the development of robust and efficient syntheses at large scale. The focus is on those parts of each synthesis related to the substrate-controlled/diastereoselective and catalytic asymmetric synthesis of epoxide intermediates and their subsequent ring-opening reactions with various nucleophiles. These are described in the form of case studies of high profile pharmaceuticals spanning a diverse range of indications and molecular scaffolds such as heterocycles, terpenes, steroids, peptidomimetics, alkaloids and main stream small molecules. Representative examples include, but are not limited to the antihypertensive diltiazem, the antidepressant reboxetine, the HIV protease inhibitors atazanavir and indinavir, efinaconazole and related triazole antifungals, tasimelteon for sleep disorders, the anticancer agent carfilzomib, the anticoagulant rivaroxaban the antibiotic linezolid and the antiviral oseltamivir. Emphasis is given on aspects of catalytic asymmetric epoxidation employing metals with chiral ligands particularly with the Sharpless and Jacobsen–Katsuki methods as well as organocatalysts such as the chiral ketones of Shi and Yang, Pages’s chiral iminium salts and typical chiral phase transfer agents.

Efficient method for ring opening of epoxides with amines by NaY zeolite under solvent-free conditions

2007 ◽  
Vol 264 (1-2) ◽  
pp. 162-169 ◽  
Author(s):  
Rukhsana Ilyas Kureshy ◽  
Surendra Singh ◽  
Noor-ul Hasan Khan ◽  
Sayed Hasan Razi Abdi ◽  
Eringathodi Suresh ◽  
...  
Keyword(s):  
Efficient Method ◽  
Ring Opening ◽  
Solvent Free ◽  
Nay Zeolite ◽  
Solvent Free Conditions ◽  
Ring Opening Of Epoxides

ChemInform Abstract: Thiourea Catalyzed Aminolysis of Epoxides under Solvent-Free Conditions. Electronic Control of Regioselective Ring Opening.

ChemInform ◽  
2010 ◽  
Vol 41 (33) ◽  
pp. no-no
Author(s):  
Swapandeep Singh Chimni ◽  
Neeraj Bala ◽  
Vaibhav A. Dixit ◽  
Prasad V. Bharatam
Keyword(s):  
Ring Opening ◽  
Solvent Free ◽  
Electronic Control ◽  
Solvent Free Conditions

Synthesis of β-amino alcohols using MgO as a new catalyst under solvent-free conditions

2008 ◽  
Vol 86 (1) ◽  
pp. 65-71 ◽  
Author(s):  
Mona Hosseini-Sarvari
Keyword(s):  
Ring Opening ◽  
Amino Alcohols ◽  
Solvent Free ◽  
Aliphatic Amines ◽  
Solvent Free Conditions ◽  
Ring Opening Of Epoxides ◽  
High Yields ◽  
Aromatic And Aliphatic Amines

MgO catalyzed efficiently the ring opening of epoxides with a range of aromatic and aliphatic amines to produce β-substituted alcohols in high yields under solvent-free conditions. Exclusive trans stereoselectivity is observed for cyclic epoxide.Key words: MgO, β-amino alcohols, solvent-free, epoxide, amine.

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