98856-64-5Relevant academic research and scientific papers
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.
Efficient synthesis of 3,4- and 4,5-dihydroxy-2-amino-cyclohexanecarboxylic acid enantiomers
Benedek, Gabriella,Palko, Marta,Weber, Edit,Martinek, Tamas A.,Forro, Eniko,Fueloep, Ferenc
scheme or table, p. 2220 - 2225 (2010/03/03)
An efficient method for the synthesis of (1S,2R,4R,5S)- and (1R,2R,4R,5S)-2-amino-4,5-dihydroxycyclohexanecarboxylic acids (-)-6 and (-)-9 and (1R,2R,3S,4R)- and (1S,2R,3S,4R)-2-amino-3,4-dihydroxycyclohexanecarboxylic acids (-)-15 and (-)-18 was develope
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.
Enzymatic resolution of alicyclic β-lactams
Kaman, Judit,Forro, Eniko,Fueloep, Ferenc
, p. 1593 - 1600 (2007/10/03)
Racemates of N-hydroxymethylated β-lactams 4-6 were resolved through the lipase-catalyzed asymmetric acylation of the primary hydroxy group at the 6S stereogenic centre. High enantioselectivity (E>200) was observed when the enzymatic reactions were perfor
Carbapenems, their production and use
-
, (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.
AN EFFICIENT SYNTHESIS OF A KEY INTERMEDIATE FOR OPTICALLY ACTIVE 5,6-CIS-CARBAPENEM ANTIBIOTICS
Tamura, Norikazu,Kawano, Yasuhiko,Matsushita, Yoshihiro,Yoshioka, Kouichi,Ochiai, Michihiko
, p. 3749 - 3752 (2007/10/02)
A versatile intermediate (18) for optically active 5,6-cis-carbapenem antibiotics was synthesized with a highly regioselective intramolecular aldol condensation as a key step.
DIVERSIFIED SYNTHETIC APPROACHES TO THE CARBAPENEM ANTIBIOTICS BASED ON SYMMETRIZATION-ASYMMETRIZATION CONCEPT
Kurihara, Masa-aki,Kamiyama, Keiji,Kobayashi, Susumu,Ohno, Masaji
, p. 5831 - 5834 (2007/10/02)
cis-Fused bicyclic β-lactam compound 9, a key intermediate to cis-substituted carbapenem antibiotics, has been synthesized in optically pure form based on symmetrization-asymmetrization concept.
STEREOCHEMICAL STUDIES 83. SATURATED HETEROCYCLES 76. PREPARATION AND CONFORMATIONAL STUDY OF PARTIALLY SATURATED 3,1-BENZOXAZINES, 3,1-BENZOXAZIN-2-ONES AND 3,1-BENZOXAZINE-2-THIONES
Bernath, Gabor,Stajer, Geza,Szabo, Angela E.,Fueloep, Ferenc,Sohar, Pal
, p. 1353 - 1366 (2007/10/02)
The cis- and trans-2-amino-4-cyclohexene-1-carboxylic acids 1 and 3 react with imidates to give the condensed-skeleton, bicyclic cis- and trans-pyrimidin-4-ones 8 and 9.The amino acids 1 and 3 were reduced to the cis- and trans-1,3-aminoalcohols 6 and 7, which were cyclized by means of imidates to the bicyclic tetrahydro-4H-3,1-benzoxazines 10 and 11, or were converted, via the corresponding carbamates 14 and 15 into the tetrahydro-4H-3,1-benzoxazin-2(1H)-ones 16 and 17.The 2-thioxo analogues 18 and 19 were prepared by cyclization of the dithiocarbamates obtained from the aminoalcohols 6 and 7 by treatment with carbon disulphide.The trans-aminoalcohol 7 and its saturated analogue reacted with p-chlorobenzaldehyde to furnish the hexahydro 13 and octahydro-4H-3,1-benzoxazine 13a, respectively. 1H and 13C NMR studies showed that, similarly to the earlier-investigated analogues containing oxygen or unsubstituted nitrogen at position 1, the synthesized cis isomers 8, 10, 16 and 18 occurred as the preferred conformer in the heterocyclic twist inverse form of N-inside type (quasiaxal C6-N bond) (B).In the trans isomers containing a saturated C-2 atom (13 and 13a), H-2 and H-6 are in cis relative positions.
