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Access to thiopyrano[2,3-b]indole via tertiary amine-catalyzed formal (3+3) annulations of β'-acetoxy allenoates with indoline-2-thiones.
Chemical Communications : Chem Comm 2017 Februrary 24
DABCO-catalyzed formal (3+3) annulations of β'-acetoxy allenoates with indoline-2-thiones are described, which provide facile access to thiopyrano[2,3-b]indole under mild reaction conditions. The reaction might proceed via the SN 2'-SN 2'-type process between β'-acetoxy allenoate and indole-2-thiolate with the assistance of the DABCO catalyst and K2 CO3 additive, followed by intramolecular Friedel-Crafts reaction at the 3-position of indole and central carbon of allene.
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