Hofmann Rearrangement of Carboxamides Mediated by N-Bromoacetamide
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.
Keywords:
Hofmann rearrangement / amides / stereoselectivity / cyclization / heterocyclesSource:
Synthesis, Stuttgart, 2016, 48, 10, 1550-1560Publisher:
- Georg Thieme Verlag Kg, Stuttgart
Funding / projects:
- Structure-activity relationship of newly synthesized biological active compound (RS-MESTD-Basic Research (BR or ON)-172032)
Note:
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3523
DOI: 10.1055/s-0035-1561405
ISSN: 0039-7881
WoS: 000375877100012
Scopus: 2-s2.0-84961231076
Collections
Institution/Community
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Jevtić, Ivana I. AU - Došen-Mićović, Ljiljana AU - Ivanović, Evica R. AU - Ivanović, Milovan PY - 2016 UR - https://cherry.chem.bg.ac.rs/handle/123456789/1935 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 VL - 48 IS - 10 SP - 1550 EP - 1560 DO - 10.1055/s-0035-1561405 ER -
@article{ author = "Jevtić, Ivana I. and Došen-Mićović, Ljiljana and Ivanović, Evica R. and Ivanović, Milovan", 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", volume = "48", number = "10", pages = "1550-1560", doi = "10.1055/s-0035-1561405" }
Jevtić, I. I., Došen-Mićović, L., Ivanović, E. R.,& Ivanović, M.. (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 L, Ivanović ER, Ivanović M. 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, Ivanović, Evica R., Ivanović, Milovan, "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 . .