Preparation of Polyfunctional Acyl Azides

Abstract

A general synthesis of acyl azides from the corresponding N-acyl benzotriazoles is described. The procedure affords acyl azides in good yields and avoids the use of acid activators and NO+ equivalents typically employed to synthesize these compounds from acid chlorides and hydrazides, respectively.

Five‐Membered Heterocycles with Three Heteroatoms: Triazoles

“…Stable and easily accessible N-acylbenzotriazoles, derived from various aliphatic, unsaturated, (hetero)aromatic, and N-protected-R-amino carboxylic acids, have been reacted with Grignard and heteroaryllithium reagents to afford the corresponding ketones [159]. A general synthesis of acyl azides from the corresponding N-acyl benzotriazoles have been described [160]. Stable and easily accessible N-aroylbenzotriazoles react with indoles in the presence of a base to afford the corresponding Naroylindoles [161].…”

A new methodology for the synthesis of N-acylbenzotriazoles

“…[1][2][3][4][5][6][7][8][9] N-acylbenzotriazoles are one of the most useful benzotriazolederivatives which have been successfully utilized to prepare numerous biologically relevant compounds under neutral and mild conditions by N-, C-, S-, and O-acylations. [10][11][12][13][14][15][16][17][18][19][20][21][22][23][24] In recent years our group has been involved in exploration of the synthetic utility of N-acylbenzotriazoles to make sugar amides by N-acylation, 25 benzoxazoles and N-phenylamides by benzotriazole ring cleavage 26,27 and ureas, carbamates and thiocarbamates by the Curtius rearrangement. 28 The earlier synthetic methods for conversion of carboxylic acids to N-acyl benzotriazole i.e.…”

Synthesis, reactivity, and electronic structure of multifarious, five-membered heteroaryl and heteroaroyl azides

“…65 Recently, a general and safe synthesis of acyl azides, including azido(2-thienyl and 2-furyl)methanones (80 and 75% yield, respectively), from the corresponding N-acyl benzotriazoles and sodium azide has been reported. 66 DSC-thermolysis of compounds 1-5 at 30-220°C in dry hexadecane for 19 min gives the corresponding isocyanates, with the sole exception of the unstable azide 4, which affords a isocyanate 2 by concomitant desilylation (Scheme 31). Otherwise, the azides 1-3 and 5 undergo similar thermal decomposition in 1-dodecanol, giving the appropriate heteroaryl carbamates in high yields (> 92 %), while the azide 5 results in a lower yield (56%), presumably due to the lesser stability of the final carbamate.…”