One-pot regioselective synthesis of functionalized and fused furans from Morita–Baylis–Hillman and Rauhut–Currier adducts of nitroalkenes

Abstract

Highly functionalized and fused furans have been synthesized via cascade reactions of Morita-BaylisHillman and Rauhut-Currier adducts of nitroalkenes with active methylene compounds. The reactions involving S N 2 0 -intramolecular Michael addition or Michael addition-intra-molecular nucleophilic substitution take place in a regioselective manner to afford synthetically and biologically useful furans in moderate to good yields.

Synthesis of β-triazolylenones via metal-free desulfonylative alkylation of N-tosyl-1,2,3-triazoles

“…In addition to their synthetic importance, these are frequently encountered as ligands in many metal complexes [32][33][34][35]. Our group has also employed 1,3-dicarbonyl compounds as binucleophiles for the construction of various carbocycles, heterocycles as well as in asymmetric catalysis [36][37][38][39][40][41][42]. Our initial objective to trap the aza vinyl rhodium carbenoid using the 1,3-dicarbonyl compounds to form pyrazolone was unsuccessful which instead led to the formation of an unexpected product, i.e.…”

α-Functionalization of Nitroalkenes and Its Applications in Organic Synthesis

“…After exploring the reactivity of RC adducts 190 with cyclic ketones 55 for the synthesis of functionalized decalins 196 (Scheme 57), interestingly, when we treated the RC adducts 190 with cyclohexanediones/dimedone 55, formation of fused furans 199 was observed instead of the expected decalins or spiro compounds (Scheme 59). 73 The reaction involves regioselective Michael addition and intramolecular nucleophilic substitution of the nitro group.…”

Synthesis of β-triazolylenones via metal-free desulfonylative alkylation of N-tosyl-1,2,3-triazoles

“…In addition to their synthetic importance, these are frequently encountered as ligands in many metal complexes [40][41][42][43]. Our group have also employed 1,3dicarbonyl compounds as binucleophiles for the construction of various carbocycles, heterocycles as well as in asymmetric catalysis [44][45][46][47][48][49][50]. Our initial objective to trap the aza vinyl rhodium carbenoid using 1,3-dicarbonyl compounds to form pyrazolone was unsuccessful which instead led to the formation of an unexpected product, i.e., β-triazolylenone.…”