An efficient, one-pot procedure for the Hofmann rearrangement of aromatic and aliphatic amides has been developed. Methyl and benzyl carbamates are produced with N-bromoacetamide in the presence of lithium hydroxide or lithium methoxide, in high yields. -Phenylamino amides gave five-membered cyclic ureas stereospecifically. Side products of aryl or benzyl bromination were minimized. This procedure offers an easy access to various protected amines or diamines, which represent important synthetic precursors.
TY - JOUR
AU - Jevtić, Ivana I.
AU - Došen-Mićović, Ljiljana I.
AU - Ivanović, Evica
AU - Ivanović, Milovan D.
PY - 2016
UR - http://aspace.agrif.bg.ac.rs/handle/123456789/4055
AB - An efficient, one-pot procedure for the Hofmann rearrangement of aromatic and aliphatic amides has been developed. Methyl and benzyl carbamates are produced with N-bromoacetamide in the presence of lithium hydroxide or lithium methoxide, in high yields. -Phenylamino amides gave five-membered cyclic ureas stereospecifically. Side products of aryl or benzyl bromination were minimized. This procedure offers an easy access to various protected amines or diamines, which represent important synthetic precursors.
PB - Georg Thieme Verlag Kg, Stuttgart
T2 - Synthesis-Stuttgart
T1 - Hofmann Rearrangement of Carboxamides Mediated by N-Bromoacetamide
EP - 1560
IS - 10
SP - 1550
VL - 48
DO - 10.1055/s-0035-1561405
ER -
@article{
author = "Jevtić, Ivana I. and Došen-Mićović, Ljiljana I. and Ivanović, Evica and Ivanović, Milovan D.",
year = "2016",
abstract = "An efficient, one-pot procedure for the Hofmann rearrangement of aromatic and aliphatic amides has been developed. Methyl and benzyl carbamates are produced with N-bromoacetamide in the presence of lithium hydroxide or lithium methoxide, in high yields. -Phenylamino amides gave five-membered cyclic ureas stereospecifically. Side products of aryl or benzyl bromination were minimized. This procedure offers an easy access to various protected amines or diamines, which represent important synthetic precursors.",
publisher = "Georg Thieme Verlag Kg, Stuttgart",
journal = "Synthesis-Stuttgart",
title = "Hofmann Rearrangement of Carboxamides Mediated by N-Bromoacetamide",
pages = "1560-1550",
number = "10",
volume = "48",
doi = "10.1055/s-0035-1561405"
}
Jevtić, I. I., Došen-Mićović, L. I., Ivanović, E.,& Ivanović, M. D.. (2016). Hofmann Rearrangement of Carboxamides Mediated by N-Bromoacetamide. in Synthesis-Stuttgart
Georg Thieme Verlag Kg, Stuttgart., 48(10), 1550-1560.
https://doi.org/10.1055/s-0035-1561405
Jevtić II, Došen-Mićović LI, Ivanović E, Ivanović MD. Hofmann Rearrangement of Carboxamides Mediated by N-Bromoacetamide. in Synthesis-Stuttgart. 2016;48(10):1550-1560.
doi:10.1055/s-0035-1561405 .
Jevtić, Ivana I., Došen-Mićović, Ljiljana I., Ivanović, Evica, Ivanović, Milovan D., "Hofmann Rearrangement of Carboxamides Mediated by N-Bromoacetamide" in Synthesis-Stuttgart, 48, no. 10 (2016):1550-1560,
https://doi.org/10.1055/s-0035-1561405 . .
