Indole-2,3-quinodimethanes: Generation, reactivity and regioselective control of intermolecular Diels-Alder reactions |
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| Authors: | Susan F. Vice Helena Nandin de Carvalho Nicholas G. Taylor Gary I. Dmitrienko |
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| Affiliation: | Guelph-Waterloo Centre for Graduate Work in Chemistry, Waterloo Campus, University of Waterloo, Waterloo, Ontario, N2L 3G1, Canada |
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| Abstract: | N-acylindole-2,3-quinodimethanes generated at low temperature from the N-acyl-2,3-bis (bromomethyl)indoles undergo a variety of cycloadditions including the reversible chelotropic reaction with sulphur dioxide to yield the unreported 1,3-dihydrothieno[3,4-b]indole-2,2-dioxide 9. Successful attempts to control the regioselectivity of reactions with unsymmetrical dienophiles are described. |
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