2021
DOI: 10.1007/s10593-021-02901-x
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[3+2] Cycloaddition reactions of 1-substituted 3,3,3-trifluoropropenes with isonitriles – synthesis of pyrroles and pyrrolines

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Cited by 3 publications
(3 citation statements)
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“…The reaction of 1-sulfonyl-and 1-sulfamoyl-(Е)-3,3,3-trifluoropropenes 1 with isocyanoacetic ester 16 in MeCN, with a catalytic amount of AgOAc added, proceeded regioselectively at room temperature, to give 3-(trifluoromethyl)-2,3-dihydro-1H-pyrroles (Δ 2 -pyrrolines) 17 in 48-75% yields (Scheme 5). 7 In the case of a reaction between alkene 1 bearing an iminosulfonyl substituent (R 1 = S(O)(NCO 2 Et)Me), the intermediate sulfoximinesubstituted pyrroline 17 underwent ring aromatization with elimination of methane(N-carbethoxy)imidosulfinic acid, resulting in the formation of ethyl 2-pyrrolecarboxylate 18 (Scheme 5). When the reaction of alkenes 1 and isocyanide 16 was performed in the presence of a base (t-BuOK) in THF, the in situ elimination of sulfur-containing fragment from cycloadducts 17 resulted in one-pot formation of pyrrole 18 (Scheme 5).…”
Section: Cycloaddition To Isocyanomethylides and Nitrile Ylides Synth...mentioning
confidence: 99%
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“…The reaction of 1-sulfonyl-and 1-sulfamoyl-(Е)-3,3,3-trifluoropropenes 1 with isocyanoacetic ester 16 in MeCN, with a catalytic amount of AgOAc added, proceeded regioselectively at room temperature, to give 3-(trifluoromethyl)-2,3-dihydro-1H-pyrroles (Δ 2 -pyrrolines) 17 in 48-75% yields (Scheme 5). 7 In the case of a reaction between alkene 1 bearing an iminosulfonyl substituent (R 1 = S(O)(NCO 2 Et)Me), the intermediate sulfoximinesubstituted pyrroline 17 underwent ring aromatization with elimination of methane(N-carbethoxy)imidosulfinic acid, resulting in the formation of ethyl 2-pyrrolecarboxylate 18 (Scheme 5). When the reaction of alkenes 1 and isocyanide 16 was performed in the presence of a base (t-BuOK) in THF, the in situ elimination of sulfur-containing fragment from cycloadducts 17 resulted in one-pot formation of pyrrole 18 (Scheme 5).…”
Section: Cycloaddition To Isocyanomethylides and Nitrile Ylides Synth...mentioning
confidence: 99%
“…When the reaction of alkenes 1 and isocyanide 16 was performed in the presence of a base (t-BuOK) in THF, the in situ elimination of sulfur-containing fragment from cycloadducts 17 resulted in one-pot formation of pyrrole 18 (Scheme 5). 7 Pyrazoline derivative 17 containing a methylsulfonyl group was used in the synthesis of 4-methanesulfonyl-3-(trifluoromethyl)pyrrolidine-2-carboxylic acid that can be considered as a fluorineand sulfur-containing analog of proline. 7…”
Section: Cycloaddition To Isocyanomethylides and Nitrile Ylides Synth...mentioning
confidence: 99%
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