Benzotriazole-mediated amidoalkylations of nitroalkanes, nitriles, alkynes and esters

Abstract

Reactions of readily available and stable N-(α-amidoalkyl)benzotriazoles 1 (derived from a variety of aliphatic, aromatic or heterocyclic aldehydes) with diverse nitroalkanes, nitriles, alkynes and esters afforded N-(β-nitroalkyl)amides 4 (54−96%), N-(β-cyanoalkyl)amides 6 (58−88%), N-acylpropargylamines 11 (41−87%) and esters of β-N-acylamino acids 13 (68−96%), respectively.

1,2,3-Triazoles

“…Novel applications of benzotriazole methodology in organic synthesis include regiospecific preparation of 1,4,5-trisubstituted pyrazoles <2007ARK(i)9> , efficient synthesis of 1,5-disubstituted tetrazoles <2007SL1204> , amidoalkylations of nitroalkanes, nitriles, alkynes, and esters <2007ARK(xi)96> , thioamidoalkylation of 1,3-dicarbonyl compounds, enol silyl ethers, and enamines <2007S1655> , C-aminoimidoylation and C-thiocarbamoylation of esters, sulfones, and ketones <2007JOC6742> , synthesis of cyano derivatives of N -alky and N -aryl piperazines <2007EJM471> , and preparation of polyfunctional acyl azides <2007JOC5802> . N -Acyl derivatives of benzotriazole are used for efficient peptide coupling of sterically hindered aminoacids <2007JOC5794> and 5-amino-1-methyl-1 H -[1,2,4]-triazole-3-carboxylic acid <2007SC1917 , expedient synthesis of N-Z -pyroglutamyl-aminoacid derivatives <2007BML6000> , synthesis of (+)-aphanorphine <2007H(72)497> , and as Mosher-Bt reagents <2007JOC4268> .…”

1-Aminoalkylphosphonium Derivatives: Smart Synthetic Equivalents of N-Acyliminium-Type Cations, and Maybe Something More: A Review

“…α-Amidoalkylation reactions play an increasingly important role in organic synthesis as convenient and effective methods for the formation of C-C and C-heteroatom bonds, particularly of the intramolecular type, allowing the synthesis of carbo- or heterocyclic systems. In most cases, N -acylimine 2 or N -acyliminium cations 3 are the correct α-amidoalkylating agents and they are generated from precursors with the relevant structure 1 ( Scheme 1 ) [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 ].…”