Intramolecular Arylation of 2-Nitrobenzenesulfonamides: A Route to Diverse Nitrogenous Heterocycles

Rearrangement of Threonine- and Serine-Based N-(3-Phenylprop-2-yn-1-yl) Sulfonamides Yields Chiral Pyrrolidin-3-ones

“…N -Substituted 2/4-nitrobenzenesulfonamides are excellent synthetic intermediates for preparing diverse nitrogenous heterocycles. , Recently, substantial attention has been paid to N -phenacyl-2/4-nitrobenzenesulfonamides derived from natural amino acids, especially serine and threonine, as the cyclization of these compounds stereoselectively yields various chiral morpholine derivatives. , On the basis of the synthetic potential of internal alkynols in the field of catalyzed intramolecular hydroalkoxylations, − we switched from N -phenacyl to N -(3-phenylprop-2-yn-1-yl) analogues and applied the previously reported reaction to potentially synthesize functionalized 1,4-oxazepanes amenable to further diversification (Scheme ).…”

Synthesis of 2‐Amino‐3‐arylindoles and their Fused Analogues via Intramolecular C‐Arylation

“…Recently, the Truce-Smiles rearrangement of natural amino acid-based 2/4nitrobenzenesulfonamides was widely investigated as a route to different nitrogen heterocycles via Cαarylation, in which CÀ H was typically activated by the adjacent carbonyl group (Scheme 1). [3][4][5][6][7][8] Inspired by this approach, we suggested the use of 2/4-nitrobenzenesulfonamides originating from 2-aminobenzyl cyanide alkylated by scaffolds without electron-withdrawing groups. Consequently, instead of undergoing Cα-arylation, these substrates may be amenable to Cγ-Scheme 1.…”

Efficient synthesis of pentasubstituted pyrroles via intramolecular C-arylation

“…It was previously demonstrated that polymer-supported α-amino acids converted into 2/4-nitrobenzenesulfonamides are an excellent pool for the synthesis of various nitrogenous heterocycles. 43,44 Recently, we focused on the application of amino acids with functionalized side chains, e.g. serine or azidoalanine, which yielded various morpholines 45 or triazolodiazepines, 46,47 respectively.…”