ChemInform Abstract: A Novel Synthesis of the 1β-Methylcarbapenem Key Intermediate Employing the (2 + 2)Cycloaddition Reaction of Chlorosulfonyl Isocyanate with a 4H-1,3-Dioxin Derivative.

ChemInform ◽  
1990 ◽  
Vol 21 (20) ◽  
Author(s):  
Y. ITO ◽  
Y. KOBAYASHI ◽  
S. TERASHIMA
Keyword(s):  
Cycloaddition Reaction ◽  
Chlorosulfonyl Isocyanate ◽  
Novel Synthesis

A Novel Synthesis of Benzopyranyl Isoxazolines: Cycloaddition Reaction of Chromone Nitrile Oxide

Heterocycles ◽  
1988 ◽  
Vol 27 (5) ◽  
pp. 1127 ◽  
Author(s):  
Jagir Singh Sandhu ◽  
Arpan K. Baruah ◽  
Dipan Prajapati ◽  
Jagir S. Sandhu
Keyword(s):  
Cycloaddition Reaction ◽  
Nitrile Oxide ◽  
Novel Synthesis

scholarly journals One-Pot Synthesis of Oxazolidinones and Five-Membered Cyclic Carbonates from Epoxides and Chlorosulfonyl isocyanate: Theoretical Evidence for the Asynchronous Concerted Pathway

2020 ◽  
Author(s):  
Esra Demir ◽  
Özlem Sarı ◽  
Yasin Çetinkaya ◽  
Ufuk Atmaca ◽  
Safiye Sağ Erdem ◽  
...  
Keyword(s):  
Potential Energy Surfaces ◽  
Density Functional ◽  
Cycloaddition Reaction ◽  
Reaction Times ◽  
Dft Method ◽  
Cyclic Carbonates ◽  
One Pot ◽  
Purification Method ◽  
Chlorosulfonyl Isocyanate ◽  
The One

The one-pot reaction of chlorosulfonyl isocyanate (CSI) with epoxides having substituted phenyl, benzyl and fused cyclic alkyl groups in different solvents under mild reaction conditions without additives and catalysts was studied. Oxazolidinones and five-membered cyclic carbonates were obtained with a ratio close to (1:1) in the cyclization reactions. The best reaction conversion for the synthesis of these compounds was carried out in dichloromethane (DCM). The method presented here has distinct advantageous over the existing methods such as one-pot reaction, shorter reaction times, metal-free reagent, good yields and very simple purification method. The mechanism for the cycloaddition reactions has been elucidated using density functional theory (DFT) method at the M06-2X/6-31+G(d,p) level. The investigation of the potential energy surfaces associated with two possible channels leading to oxazolidinones and five-membered cyclic carbonates revealed that the cycloaddition reaction takes place through an asynchronous concerted mechanism in gas phase and in DCM.

scholarly journals One-pot synthesis of oxazolidinones and five-membered cyclic carbonates from epoxides and chlorosulfonyl isocyanate: theoretical evidence for an asynchronous concerted pathway

2020 ◽  
Vol 16 ◽  
pp. 1805-1819
Author(s):  
Esra Demir ◽  
Ozlem Sari ◽  
Yasin Çetinkaya ◽  
Ufuk Atmaca ◽  
Safiye Sağ Erdem ◽  
...  
Keyword(s):  
Potential Energy Surfaces ◽  
Density Functional ◽  
Cycloaddition Reaction ◽  
Reaction Times ◽  
Dft Method ◽  
Synthetic Approach ◽  
Cyclic Carbonates ◽  
One Pot ◽  
Purification Method ◽  
Chlorosulfonyl Isocyanate

The one-pot reaction of chlorosulfonyl isocyanate (CSI) with epoxides having phenyl, benzyl and fused cyclic alkyl groups in different solvents under mild reaction conditions without additives and catalysts was studied. Oxazolidinones and five-membered cyclic carbonates were obtained in ratios close to 1:1 in the cyclization reactions. The best yields of these compounds were obtained in dichloromethane (DCM). Together with 16 known compounds, two novel oxazolidinone derivatives and two novel cyclic carbonates were synthesized with an efficient and straightforward method. Compared to the existing methods, the synthetic approach presented here provides the following distinct advantageous: being a one-pot reaction with metal-free reagent, having shorter reaction times, good yields and a very simple purification method. Moreover, using the density functional theory (DFT) method at the M06-2X/6-31+G(d,p) level of theory the mechanism of the cycloaddition reactions has been elucidated. The further investigation of the potential energy surfaces associated with two possible channels leading to oxazolidinones and five-membered cyclic carbonates disclosed that the cycloaddition reaction proceeds via an asynchronous concerted mechanism in gas phase and in DCM.

scholarly journals Novel synthesis of highly functionalized cyclopentane derivatives via [3 + 2] cycloaddition reactions of donor–acceptor cyclopropanes and (E)-3-aryl-2-cyanoacrylates

2019 ◽  
Vol 43 (1-2) ◽  
pp. 43-49 ◽  
Author(s):  
Chenlu Dai ◽  
Mingshuang Li ◽  
Mengjun Chen ◽  
Naili Luo ◽  
Cunde Wang
Keyword(s):  
Cycloaddition Reaction ◽  
Cycloaddition Reactions ◽  
X Ray ◽  
X Ray Crystallography ◽  
Novel Synthesis ◽  
Donor Acceptor

An efficient [3 + 2] cycloaddition reaction of cyanocyclopropanecarbonates and ( E)-3-aryl-2-cyanoacrylates mediated by 1,8-diazabicyclo[5.4.0]undec-7-ene for the synthesis of highly functionalized cyclopentane derivatives in moderate to good yields (79%−87%) was developed. The structures of two typical products were confirmed by X-ray crystallography.

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