766-36-9Relevant articles and documents
Pyrrolinone compound and synthesis method thereof
-
, (2021/04/03)
The invention provides a pyrrolinone compound, the structural formula of the pyrrolinone compound is shown as the formula 1, R1 is selected from one of C1-C5 alkoxy, benzyloxy, C1-C5 alkyl and phenyl;R2 and R3 are respectively and independently selected from one of hydrogen, a C1-C5 alkyl group, a C1-C5 alkoxy group, a C1-C5 alkyl sulfenyl group, a C1-C5 alkyl sulfinyl group, a C1-C5 alkyl sulfonyl group, a phenyl group with different substitutions, a phenoxy group with different substitutions, a thiophenyl group with different substitutions, a benzenesulfinyl group with different substitutions and a benzenesulfonyl group with different substitutions; and n1 and n2 are integers from 1 to 5. The pyrrolinone compound can be used as pharmaceutical intermediates. The invention also provides asynthesis method of the pyrrolinone compound. The method is more suitable for industrialization, lower in cost and milder in synthesis condition.
Scalable Synthesis of 3-Ethyl-4-methyl-1,5-dihydro-2 H -pyrrol-2-one: An Important Building Block of the Antidiabetic Drug Glimepiride
Chavan, Subhash P.,Pawar, Ambaji A.,Patil, Niteen B.,Kadam, Appasaheb L.,Shinde, Shrikrishna S.
, p. 3480 - 3484 (2020/09/15)
A four-step, practical, and easily scalable synthesis of 3-ethyl-4-methyl-1,5-dihydro-2H-pyrrol-2-one, an important building block of the antidiabetic drug glimepiride, has been accomplished. Key features are the synthesis of 3-methyl-4-hydroxy-2-butenolide in water and triflic acid mediated N-benzyl lactam N-deprotection. The main advantages of this process are the scalable synthetic route and decreased number of reaction steps, which paves the way for the industrial-scale synthesis of 3-ethyl-4-methyl-1,5-dihydro-2H-pyrrol-2-one.
Synthesis of 3-Ethyl-4-methyl-1,5-dihydro-2H-pyrrol-2-one by Novel Palladium(II)-Catalyzed Cyclization and Ring-Closing Metathesis
Chavan, Subhash P.,Pathak, Ashok B.,Pawar, Kailash P.
, p. 955 - 960 (2015/03/30)
Synthesis of 3-ethyl-4-methyl-1,5-dihydro-2H-pyrrol-2-one is described starting from commercially available allylamine and 4-methoxybenzylamine employing palladium-catalyzed cyclization or ring-closing metathesis as the key steps.
Synthesis and properties of mesobilirubins XIIγ and XIIIγ and their mesobiliverdins
Sabido, Portia Mahal G.,Lightner, David A.
, p. 775 - 789 (2014/05/20)
The title pigments, with propionic acid groups displaced to the lactam end rings, were synthesized for the first time by the "1 + 2 + 1" approach, coupling two equivalents of a monopyrrole to a dipyrrylmethane (to give XIIγ), or the "2 + 2" approach, self-coupling two equivalents of a dipyrrinone (to give XIIIγ). Using the "1 + 2 + 1" approach, mesobilirubin IIIα was also prepared. Mesobilirubins XIIγ and XIIIγ are more polar than mesobilirubin IIIα and unlike IIIα cannot effectively engage the propionic acid groups in intramolecular hydrogen bonding to the dipyrrinone components. The new mesobilirubins give exciton coupled circular dichroism spectra in the presence of human serum albumin or quinine, with the XIIγ isomer exhibiting Cotton effect intensities nearly as strong as those from the IIIα isomer; whereas, the XIIIγ isomer exhibits far weaker intensities. Mesobilirubin IIIα requires glucuronidation for hepatobiliary elimination; whereas, XIIγ and XIIIγ do not, and they are excreted intact across the liver into bile. The corresponding biliverdins XIIγ and XIIIγ are reduced only slowly by biliverdin IXα reductase, in contrast to the fast reduction of the natural IXα isomer. Graphical abstract: [Figure not available: see fulltext.]
Regiocontrolled synthesis of pyrrole-2-carboxaldehydes and 3-pyrrolin-2-ones from pyrrole Weinreb amides
Coffin, Aaron R.,Roussell, Michael A.,Tserlin, Elina,Pelkey, Erin T.
, p. 6678 - 6681 (2007/10/03)
A regiocontrolled synthesis of 3,4-disubstituted pyrrole-2-carboxaldehydes was completed in two steps from acyclic starting materials. A Barton-Zard pyrrole synthesis between N-methoxy-N-methyl-2-isocyanoacetamide and α-nitroalkenes or β-nitroacetates provided N-methoxy-N-methyl pyrrole-2-carboxamides (pyrrole Weinreb amides), which were converted into the corresponding pyrrole-2-carboxaldehydes by treatment with lithium aluminum hydride. A regioselective oxidation of the pyrrole-2-carboxaldehydes gave the corresponding 3,4-disubstituted 3-pyrrolin-2-ones.
A facile synthesis of 3,4-disubstituted-1,2-dihydro-5H-pyrrol-2-ones
Bhandari, Kalpana,Sharma
, p. 2467 - 2470 (2007/10/03)
A facile and efficient method for the synthesis of 3,4-disubstituted-1,2- dihydro-5H-pyrrol-2-ones 8a,c-f is reported. The method involves the hydrogenation of cyanohydrins of 2-alkyl-3-oxobutyric acid alkyl esters 1a-f, over Raney Ni at 50 psi to furnish hitherto unknown aminoacetyl intermediates 6a-f in quantitative yields which are cyclised to the targeted compounds.
Total synthesis of cis and trans-hydroxyglimepiride: Active metabolite of glimepiride
Gurjar, Mukund K.,Joshi, Ramesh A.,Chaudhuri, Siddhartha R.,Joshi, Shreerang V.,Barde, Anup R.,Gediya, Lalji K.,Ranade, Prasad V.,Kadam, Suresh M.,Naik, Sanjay J.
, p. 4853 - 4855 (2007/10/03)
Syntheses of trans-hydroxyglimepiride 2b, a human metabolite of the blood glucose lowering agent glimepiride 1 and its corresponding cis-stereoisomer 2a, are described.
An intramolecularly hydrogen bonded dihydrotripyrrinone
Tipton, Adrianne K.,Lightner, David A.
, p. 425 - 440 (2007/10/03)
A yellow tripyrrole analog (1) of bilirubin has been synthesized, and its lone propionic acid group is found to engage in conformation determining, intramolecular hydrogen bonding in solution and in the crystal. Molecular modelling and X-ray crystallography reveal an abbreviated ridge-tile or L-shape conformation in which an essentially planar dipyrrinone is hydrogen bonded to the single opposing propionic acid group. In the (arbitrary) (P)-helicity ridge-tile, the torsion angles about C(10) are computed to be 55° and 61° by molecular dynamics and found to be 66° and 53° in the crystal. Such torsion angles lead to an interplanar dihedral angle (～93°) between the dipyrrinone and its adjoining pyrrole that is very close to the dihedral angle (～98°) found in intramolecularly hydrogen bonded bilirubin.
Diastereoselective Synthesis of Phycocyanobilin-Cysteine Adducts
Bishop, John E.,Nagy, Jon O.,O'Connell, John F.,Rapoport, Henry
, p. 8024 - 8035 (2007/10/02)
Methodology is presented for the synthesis of two diastereomers of a cysteine-linked phycocyanobilin derivative. The crucial reaction is a diastereoselective 1,6-Michael addition of cysteine methyl ester to an appropriate dihydropyrromethenone educt. The diastereomers so generated were then elaborated to two phycocyanobilin trimethyl esters. Definitive assignments of relative stereochemistry, double bond geometry, and solution conformation are accomplished by application of ROESY NMR experiments, while absolute stereochemical assignments are based on degradation to compounds of known chirality.
Relative Stereochemistry of the A Ring of Plant Bile Pigments
Schoenleber, Robert W.,Kim, Youseung,Rapoport, Henry
, p. 2645 - 2651 (2007/10/02)
The synthesis and characterization, including the stereochemistry, of a series of 3,4-dihydropyrromethenones and 2,3-dihydrodioxobilins are described.High-resolutions 1H NMR spectral analysis allows the determination of the A ring coupling constants for a series of cis and trans model compounds.From these data and correlations, the relative stereochemistry in the A ring of phycocyanin and similar bile pigment structures can be concluded.
