- Spontaneous Dimerization of Allenes in Situ: An Efficient Synthesis of Substituted 1,2-Dimethylenecyclobutanes with High Regio- and Stereoselectivities
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An intermolecular [2+2] cycloaddition reaction for the synthesis of 1,2-dimethylenecyclobutane derivatives from the commercially available starting materials aryl acetylenes, nBuLi, formamides, and trimethylsilyl cyanide (TMSCN) has been achieved. This reaction displays high regio- and stereoselectivities due to the captodative effect. The mechanism of the reaction has been investigated by the deuterium labeling experiments and DFT calculations. Cycloaddition of captodative allenes: A regio- and stereoselective intermolecular [2+2] cycloaddition of captodative allenes (in situ generated) for the efficient synthesis of substituted 1,2-dimethylenecyclobutanes is disclosed (see scheme; TMS = trimethylsilyl). The mechanism of the reaction has been investigated by deuterium labeling experiments and the selectivity has been studied by DFT calculations.
- Miao, Maozhong,Wang, Wenmin,Yang, Weijun,Xu, Lijun,Ma, Jing,Ren, Hongjun
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- Acyl Cyanides as Bifunctional Reagent: Application in Copper-Catalyzed Cyanoamidation and Cyanoesterification Reaction
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Cu-catalyzed domino decyanation and cyanation reaction of acyl cyanides with amines or alcohols have been developed. The cyano sources were generated in situ via C-CN cleavage yielding the corresponding cyano substituted amides or esters in moderate to excellent yields. This approach features a cheap copper catalyst, domino decyanation and cyanation reaction, readily available starting materials, broad substrate scope, operational simplicity, and the potential for further transformation of the cyano group.
- Chen, Zhengwang,Wen, Xiaowei,Zheng, Weiping,He, Ruolan,Chen, Dou,Cao, Dingsheng,Long, Lipeng,Ye, Min
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supporting information
p. 5691 - 5701
(2020/04/10)
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- Bacterial cell leakage potential of newly synthesized quinazoline derivatives of 1,5-benzodiazepines analogue
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Novel quinazoline embellished analogues of 1,5-benzodiazepine (6, 9, 13, 17, 21 and 24) were synthesized using one-pot domino approach. Structure of the compounds synthesized, were established with the help of IR, 1H NMR, 13C NMR and
- Dwivedi, Jaya,Kishore, Dharma,Misra, Apoorva,Sharma, Swapnil,Shukla, Shruti
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- A process for preparing β - cyano compound styrene-isobutene method (by machine translation)
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The invention discloses a on the isobutene β - cyano styrene synthetic method of the compound. The method utilizes a cinnamic acid compounds and azo azobisisobutyronitrile as reaction raw material, the ferric iron catalytic, in the acetonitrile solution in heating by the reaction to the isobutene escapes suosuo the coupling β - cyano styrenic compound. The preparation method of the raw material, cheap and easily obtained catalyst, mild reaction system, the operation is simple, non-ligand, alkali, such as participation of the oxidizing agent. At the same time, use of non-toxic azo azobisisobutyronitrile as a cyano source, has outstanding safety, green and environmental protection. (by machine translation)
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Paragraph 0023; 0025; 0027; 0028; 0029; 0031; 0033
(2017/07/22)
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- βUnsaturated acyl cyanides as new bis-electrophiles for enantioselective organocatalyzed formal [3+3]spiroannulation
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α,β-Unsaturated acyl cyanides are key bis-electrophile substrates for successful domino enantioselective organocatalyzed Michael-intramolecular acylation domino sequences. This new reactivity has been applied to the synthesis of enantioenriched azaspiro[4
- Goudedranche, Sebastien,Bugaut, Xavier,Constantieux, Thierry,Bonne, Damien,Rodriguez, Jean
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supporting information
p. 410 - 415
(2014/04/03)
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- ETHYLENIC ACYL CYANIDES II: CONJUGATE ADDITION OF ALKYNYLSILANES TO ETHYLENIC ACYL CYANIDES.
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3-Alkynylacyl cyanides or 3-alkynylacids and their esters can be obtained by a conjugate addition of alkynylsilanes to α,β-ethylenic acyl cyanides.
- Jellal, Abdelkebir,Zahra, Jean-Pierre,Santelli, Maurice
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p. 1395 - 1398
(2007/10/02)
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- Synthesis of α,β-Unsaturated and Other Reactive Acyl Cyanides
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Reaktive aliphatische Acylcyanide (1 - 10, siehe Tab. 1) werden aus Acylchloriden, Natriumiodid und Kupfer(I)-cyanid unter verschiedenen Bedingungen dargestellt.Die Reaktion verlaeuft ueber die Acyliodide.
- Hoffmann, H. M. R.,Haase, Klaus,Ismail, Zeinhom M.,Preftitsi, Stamatia,Weber, Anette
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p. 3880 - 3885
(2007/10/02)
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- TRIBUTYLTIN CYANIDE: A FACILE CYANATING AGENT OF ACYL CHLORIDES
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Tributyltin cyanide was prepared from tributyltin chloride and potassium cyanide, and was found to be an efficient cyanation reagent for acyl chlorides to give acyl cyanides in excellent yields.
- Tanaka, Masato
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p. 2959 - 2962
(2007/10/02)
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