2016
DOI: 10.1016/j.tetlet.2016.06.063
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Wittig–Horner mediated synthesis of 4-vinyl sulfide derivatives of pyrazoles

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Cited by 10 publications
(4 citation statements)
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“…On the other hand, the vinyl sulfones P5 and P6 were successfully synthesized in good yields (78% and 75%, respectively) by oxidation of the vinyl suldes P1 and P2 with mCPBA. As observed in a previous work, 31,40 the oxidation reaction caused the isomerization of the Z isomers, yielding the sulfones as single E isomers. The dyes P1-P6 were fully characterized by 1 H and 13 C NMR, FTIR, highresolution mass spectrometry (HRMS) or elemental analysis.…”
Section: Synthesissupporting
confidence: 73%
See 1 more Smart Citation
“…On the other hand, the vinyl sulfones P5 and P6 were successfully synthesized in good yields (78% and 75%, respectively) by oxidation of the vinyl suldes P1 and P2 with mCPBA. As observed in a previous work, 31,40 the oxidation reaction caused the isomerization of the Z isomers, yielding the sulfones as single E isomers. The dyes P1-P6 were fully characterized by 1 H and 13 C NMR, FTIR, highresolution mass spectrometry (HRMS) or elemental analysis.…”
Section: Synthesissupporting
confidence: 73%
“…[31][32][33][34][35][36][37][38] In this regard, our continuous interests in the synthesis of organochalcogen compounds prompted us to access symmetrical and unsymmetrical vinyl suldes by a straightforward approach, using a Wittig-Horner reaction, as precursors of products carrying a higher oxidation state on sulfur. 39,40 In this sense, photoactive divinyl suldes and sulfones have been obtained. 31,41 However, there is a lack of information on the rationalization of comparative electronic effects exerted by organosuldes, sulfoxides and sulfones on excited and ground states of pushpull p-conjugated structures.…”
Section: Introductionmentioning
confidence: 99%
“…On the other hand, the required sulfur reagent 2 a and its congener 2 b were efficiently synthesized from (diphenyl phosphoryl)methyl 4‐methyl benzenesulfonate ( 5 ) [14a] in 92 and 78 % yield, respectively, as bench stable solids (Scheme 3).…”
Section: Resultsmentioning
confidence: 99%
“…Silylation of diphenyl phosphite using BSTFA, followed by Abramov reaction with paraformaldehyde at 90 °C provided the silyl ether 32 (Table , entry 1). Whereas silyl phosphites react readily with simple aliphatic aldehydes at room temperature, reactions of phosphonates (other than methyl) with paraformaldehyde typically require more forcing conditions . Trioxane was investigated as an alternative source of formaldehyde, but it failed completely to react in the Abramov reaction (entry 2).…”
Section: Results and Discussionmentioning
confidence: 99%