Silver‐Catalyzed Efficient Synthesis of Oxindoles and Pyrroloindolines via α‐Aminoalkylation of N‐Arylacrylamides with Amino Acid Derivatives

Abstract

α-Aminoalkylation of N-arylacrylamides with amino acid derivatives was achieved by silver-catalysis in moderate to high yields. The reaction provides an efficient strategy for the synthesis of functionalized oxindoles, and is suitable for a wide range of N-arylacrylamides and amino acids, both of which are inexpensive and readily available. The oxindoles obtained were readily transformed into densely functionalized pyrroloindolines by deprotection and cyclization in one pot.

α‐Amino Acid Sulfonamides as Versatile Sulfonylation Reagents: Silver‐Catalyzed Synthesis of Coumarins and Oxindoles by Radical Cyclization

“…Finally, catalytic sulfonylation of 1x was also achieved and provided isoquinolinedione 3x in 50 % yield. In contrast to our recent silver‐catalyzed α‐aminoalkylation reaction, no products derived from the addition of α‐aminoalkyl radical to the N ‐acryl amides were observed.…”

Syntheses of 3,3-Disubstituted Dihydrobenzofurans, Indolines, Indolinones and Isochromanes by Palladium-Catalyzed Tandem Reaction Using Pd(PPh3)2Cl2/(±)-BINAP as a Catalytic System

“…The domino reactions of the synthesis of them were summarized mainly as follows: (i) the Pd or Ni-catalyzed cyclocarbopalladation/coupling fractions, in which the process was initiated by Heck cyclization of a starter (halide) and a relay (alkene), followed by intermolecular coupling reactions with a terminator (organometallic reagents, alkenes, alkynes, etc. ), including Suzuki, Stille, Heck, Sonogashira, C-H activation, carbonylation and amination and so forth [15][16][17]22,24,25,[29][30][31][32][33][34][35][36][37][38][39][40][41][42][43][44]; (ii) the C-H oxidative radical coupling reactions, in which these transformations were based on tandem radical addition/cyclization in the presence of oxidants with/without metal catalysts [18][19][20][21]23,26,[45][46][47][48][49][50][51][52][53][54][55]; and (iii) the other reactions [24,[56][57][58][5...…”

gem-Bromonitrocyclobutane induced radical cyclization of acrylanilides to construct 2-oxindolesviaphotoredox catalysis

“…13 A potential application of our method to the synthesis of pyrroloindoline structures is shown in Scheme 2, which are motifs in many pharmaceuticals and natural products. 15 A control experiment was carried out to get some insights into the reaction mechanism (Scheme 3). Under the standard conditions, 2.0 equiv.…”

“…13 A potential application of our method to the synthesis of pyrroloindoline structures is shown in Scheme 2, which are motifs in many pharmaceuticals and natural products. 15…”