98856-64-5Relevant articles and documents
A convenient Hofmann reaction of carboxamides and cyclic imides mediated by trihaloisocyanuric acids
Bastos, Gustavo A.,de Mattos, Marcio C.S.
, (2021/09/29)
A simple, efficient and pot-economic approach in a single vessel has been developed for conversion of aromatic and aliphatic carboxamides into primary amines with one fewer carbom atom (Hofmann reaction) in 38–89 % yield by reacting with trichloro- or tribromoisocyanuric acid and sodium hydroxide in aqueous acetonitrile. Under the same reaction conditions, cyclic imides gave amino acids (69–83 %). The role of the trihaloisocyanuric acids is the in situ generation of N-haloamides, key-intermediates for the Hofmann reaction. The scalability of the methodology was demonstrated by a multigram-scale transformation of phthalimide into anthranilic acid in 77 % yield.
Synthesis of β-lactams bearing functionalized side chains from a readily available precursor
Lee, Myung-Ryul,Stahl, Shannon S.,Gellman, Samuel
supporting information; experimental part, p. 5317 - 5319 (2009/06/18)
(Chemical Equation Presented) The reaction of chlorosulfonyl isocyanate (CSI) with alkenes provides β-lactams in quantity, and the products have frequently been used for ring-opening polymerization to generate nylon-3 materials. Prior uses of this approach have focused almost entirely on β-lactams with purely hydrocarbon substitutents. We show how a variety of β-lactams bearing protected polar substituents can be generated from CSI-derived building blocks.
Carbapenems, their production and use
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, (2008/06/13)
A compound of the general formula: STR1 wherein X is a lower alkylene group which may optionally be substituted by a hydroxyl group, or a lower alkenylene group, Y is (1) a lower alkyl group, (2) a cycloalkyl group containing 3 to 8 carbon atoms, (3) a lower alkenyl group, (4) an aryl group, (5) an aralkyl group or (6) a 3- to 8-membered heterocyclic group, or the partial structural formula Y--SO2 --X--, with X and Y being combined with each other, represents a group of the formula: STR2 wherein l is an integer of 0 to 3, and m and n each is an integer of 0 to 6, provided that the sum of m and n is in the range of 2 to 6, and R is a hydrocarbon group which may optionally be substituted or a 3- to 8-membered heterocyclic group, or a pharmaceutically acceptable salt thereof a method of production thereof and use thereof. The compound (I) has antimicrobial and β-lactamase inhibitory activities.