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dispiropyrrolidine
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A one-pot, three-component regiospecific synthesis of dispiropyrrolidines containing a thiophenone ring via 1,3-dipolar cycloaddition reactions of azomethine ylides
, Article Tetrahedron Letters ; Volume 54, Issue 20 , May , 2013 , Pages 2520-2524 ; 00404039 (ISSN) ; Khodabakhshi, M. R ; Ghahremannejad, Z ; Foroushani, B. K ; Ng, S. W ; Sharif University of Technology
2013
Abstract
The synthesis of new dispiropyrrolidines containing a thiophenone ring has been achieved by a one-pot, three-component 1,3-dipolar cycloaddition reaction. Unsaturated thiophenone dipolarophiles were reacted with azomethine ylides, generated in situ from sarcosine and cycloketone derivatives (isatin, ninhydrin, acenaphthoquinone), to produce the corresponding cycloadducts in good yields (70-90%). The cycloaddition reaction was found to be highly regio- and diastereoselective
One-pot synthesis of dispiro[oxindole-3,3′-pyrrolidines] by three-component [3+2] cycloadditions of in situ-generated azomethine ylides with 3-benzylidene-2,3-dihydro-1H-indol-2-ones
, Article Helvetica Chimica Acta ; Volume 96, Issue 11 , 2013 , Pages 2103-2114 ; 0018019X (ISSN) ; Kiamehr, M ; Reza Khodabakhshi, M ; Jebeli Javan, M ; Fathi, S ; Villinger, A ; Iaroshenko, V. O ; Langer, P ; Sharif University of Technology
2013
Abstract
An efficient one-pot, three-component synthesis of novel dispiro[oxindole-3,3′-pyrrolidines] by 1,3-dipolar cycloaddition of azomethine ylides, in situ generated by reaction of 1,2-diones with sarcosine and subsequent decarboxylation, with a series of (E)-3-benzylidene-2,3-dihydro- 1H-indol-2-ones is reported. Molecular complexity is generated in only one synthetic step. All reactions proceed with excellent regioselectivity and in good-to-excellent yields. The workup is easy, the reaction times are short, and no catalyst is required. © 2013 Verlag Helvetica Chimica Acta AG, Zürich