A New, Fast and Easy Strategy for One‐pot Synthesis of Full Substituted Cyclopropanes: Direct Transformation of Aldehydes to 3‐Aryl‐1,1,2,2‐tetracyanocyclopropanes

Crossed one-pot reaction of mixed cyclic b-dicarbonyl with various aldehydes in the presence of cyanogen bromide and triethylamine leads to the selective and efficient formation of crossed new unsymmetrical spiro dihydrofurans at room temperature. The products were obtained in good to excellent yields. Structure elucidation was carried out by 1 H NMR, 13 C NMR, FT-IR spectroscopy, Mass analyses and X-ray crystallography technique. A proposed mechanism was discussed for the formation of products. ArticleNoroozi Pesyan et al. Scheme 1 One-pot cascade selective reaction of the mixture of an aldehyde (4a-4e) and two different cyclic b-dicarbonyl compounds Scheme 2 One-pot cascade selective reaction of 1 and 2 with 4 (top), 2 and 3 with 4 (bottom) in the presence of BrCN and triethylamine Scheme 3 Mechanism of the formation of 6a as a representative

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Regioselective One‐pot Synthesis of New Unsymmetric Spiro Dihydrofurans in the Reaction of Mixed Two Different Cyclic β‐Dicarbonyl Compounds with BrCN and Aldehydes in the Presence of Et₃N

Pesyan

Shokr

Gharib

et al. 2015

J Chinese Chemical Soc

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Synthesis of Bis‐spiro Cyclopropanes Based on Meldrum’s Acid by Milling

Kashani

Pesyan

Tunç

et al. 2015

J Chinese Chemical Soc

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Reaction of 2,2-dimethyl-1,3-dioxane-4,6-dione (Meldrum's acid) with various solid aldehydes in the presence of cyanogen bromide and solid sodium ethoxide (EtONa) leads to the selective and efficient formation of bis-spiro cyclopropanes based on Meldrum's acid at the range of 0°C to room temperature. The products were obtained in good to excellent yields. Structure elucidation is carried out by 1 H NMR, 13 C NMR, FT-IR spectroscopy, mass analyses and X-ray crystallography techniques. A possible mechanism for the formation of products is also discussed under solvent-free condition.

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One‐pot, fast cyclopropanation reaction of indandione with various aldehydes in the presence of cyanogen bromide and trimethylamine

Aalinejad

Pesyan

2019

J Chinese Chemical Soc

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A new, fast, and easy one‐pot cyclopropanation reaction of aromatic and aliphatic aldehydes with 1H‐indene‐1,3(2H)‐dione and cyanogen bromide (BrCN) was developed for synthesizing 3′‐(aryl[alkyl])‐dispiro[indan‐2,1′‐cyclopropane‐2′,2′′‐indan]‐1,1′′,3,3′′‐tetrone in excellent yields in a short time (about 15 s) under basic media. All structures were characterized using IR, 1H NMR, and 13C NMR spectroscopy techniques.

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A New, Fast and Easy Strategy for One‐pot Synthesis of Full Substituted Cyclopropanes: Direct Transformation of Aldehydes to 3‐Aryl‐1,1,2,2‐tetracyanocyclopropanes

Cited by 13 publications

References 26 publications

Regioselective One‐pot Synthesis of New Unsymmetric Spiro Dihydrofurans in the Reaction of Mixed Two Different Cyclic β‐Dicarbonyl Compounds with BrCN and Aldehydes in the Presence of Et₃N

Regioselective One‐pot Synthesis of New Unsymmetric Spiro Dihydrofurans in the Reaction of Mixed Two Different Cyclic β‐Dicarbonyl Compounds with BrCN and Aldehydes in the Presence of Et₃N

Synthesis of Bis‐spiro Cyclopropanes Based on Meldrum’s Acid by Milling

One‐pot, fast cyclopropanation reaction of indandione with various aldehydes in the presence of cyanogen bromide and trimethylamine

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A New, Fast and Easy Strategy for One‐pot Synthesis of Full Substituted Cyclopropanes: Direct Transformation of Aldehydes to 3‐Aryl‐1,1,2,2‐tetracyanocyclopropanes

Cited by 13 publications

References 26 publications

Regioselective One‐pot Synthesis of New Unsymmetric Spiro Dihydrofurans in the Reaction of Mixed Two Different Cyclic β‐Dicarbonyl Compounds with BrCN and Aldehydes in the Presence of Et3N

Regioselective One‐pot Synthesis of New Unsymmetric Spiro Dihydrofurans in the Reaction of Mixed Two Different Cyclic β‐Dicarbonyl Compounds with BrCN and Aldehydes in the Presence of Et3N

Synthesis of Bis‐spiro Cyclopropanes Based on Meldrum’s Acid by Milling

One‐pot, fast cyclopropanation reaction of indandione with various aldehydes in the presence of cyanogen bromide and trimethylamine

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Product

Resources

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Regioselective One‐pot Synthesis of New Unsymmetric Spiro Dihydrofurans in the Reaction of Mixed Two Different Cyclic β‐Dicarbonyl Compounds with BrCN and Aldehydes in the Presence of Et₃N

Regioselective One‐pot Synthesis of New Unsymmetric Spiro Dihydrofurans in the Reaction of Mixed Two Different Cyclic β‐Dicarbonyl Compounds with BrCN and Aldehydes in the Presence of Et₃N