2000
DOI: 10.1021/jo000792f
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N-Acylbenzotriazoles:  Neutral Acylating Reagents for the Preparation of Primary, Secondary, and Tertiary Amides

Abstract: Readily available N-acylbenzotriazoles 2a-q efficiently acylate aqueous ammonia and primary and secondary amines to give primary, secondary, and tertiary amides in good to excellent yields. The wide applicability of the procedure is illustrated by the preparation of (i) alpha-hydroxyamides from alpha-hydroxy acids and of (ii) perfluoroalkylated amides.

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Cited by 208 publications
(120 citation statements)
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“…69 Katritzky and coworkers have suggested N-acyl-benzotriazoles as useful acylating reagents for amines. 70 Acyl isothiocyanates are also used as acylating agents in different reactions. Recently our group has reported a chemoselective N-benzoylation of aminophenols using benzoyl isothiocyanates as acylating agents.…”
Section: Acyl Isothiocyanates As Acylating Agentsmentioning
confidence: 99%
“…69 Katritzky and coworkers have suggested N-acyl-benzotriazoles as useful acylating reagents for amines. 70 Acyl isothiocyanates are also used as acylating agents in different reactions. Recently our group has reported a chemoselective N-benzoylation of aminophenols using benzoyl isothiocyanates as acylating agents.…”
Section: Acyl Isothiocyanates As Acylating Agentsmentioning
confidence: 99%
“…Since 1985, he has published more than 300 papers and several reviews dealing with benzotriazole. [5][6][7][8][9][10][11] He defined benzotriazole as a compound which fulfils all demands of an ideal synthetic auxiliary: it is inexpensive, stable, it can be introduced readily at the beginning of the reaction sequence, it is stable during various synthetic operations, it exerts an activating influence on the other parts of the molecule, it is easy to remove and can be recovered and used again. 12 Our group started with benzotriazole chemistry in 1977 and the results have been published in more than 30 papers.…”
Section: Introductionmentioning
confidence: 99%
“…10a-c Aminoxy peptides also feature strong intramolecular hydrogen bonds between adjacent residues in peptidomimetic foldamers 11 and may provide useful labels. N-Acylbenzotriazoles are easily prepared, non-hygroscopic, chirally stable analogs of acid halides that are relatively insensitive to water, 12,13 and are therefore advantageous for N-, O-, C-, or S-acylation; [12][13][14][15][16][17][18] especially where the corresponding acid chlorides are unstable or difficult to prepare. 19,20 We previously acylated amino acids and amines with N-(4-arylazobenzoyl)-1H-benzotriazoles 21 and we recently synthesized azodye-labeled peptides in good yields by a milder procedure than published methods.…”
Section: Introductionmentioning
confidence: 99%