1.5- Dihydro-2//-pyrrole-2-ones

Keywords isocyanide, chalcone, 5-hydroxy-3,5-diary I-1,5-dihydro-2//-pyrrol-2-one... 

Diimino-thietane-2-carboxylic acid derivatives has been detected as an intermediate in synthesis of 4-amino-5-thioxo-l,5-dihydro-pyrrol-2-ones from ethyl mercaptoacetate and oxalodiimidoyl dichloride <2006JOC2332> (Scheme 29). 

Benzoyl-l-phenyl-5-methoxycarbonyl-2,3-dihydro-pyrrole-2,3-dione was reacted with 5/5-dimethyl-3-p-methoxyphenylamino-2-cyclohexen-l-one in boiling benzene to afford 6,6-d imethyl-1 -p-methoxyphenyl-2,4-dioxo-2,3,4,5,6,7-hexahydro-lH-indole-3-spiro-2-(3-benzoyl-5-oxo-4-phenyl-amino-2,5-dihydrofuran) in high yield. The reaction proceeded by the enamine addition to the 2-carbonyl group with ring opening, followed by double cyclization (06RJOC772). 

Bouillon, J.P. Tinant, B. Nuzillard, J.M. Portella, C. Synthesis of new 3-(l-ethylsulfanyl-2-perfluoroalkyl)-5-hydroxy-5-methyl 5-phenyl)-l,5-dihydro-pyrrol-2-ones starting from y-keto thioesters and imines. Synthesis 2004, 711-721. 

Thieno[2,3-d ]pyrimidin-4(3 H) -one, 3-methyl-synthesis, 4, 1017 Thieno[2,3-d ]pyrimidin-4-ones synthesis, 4, 1017, 1018, 1022 Thieno[2,3-6]pyrrole, 5-aryl-synthesis, 6, 1009 Thieno[2,3-6]pyrrole, N-benzyl- H NMR, 4, 1042 UV spectra, 4, 1044 Thieno[2,3-c]pyrrole, N-ethyl-UV spectra, 4, 1044 Thieno[3,2-6]pyrrole, 5-aryl-synthesis, 6, 1009 Thieno[3,2-6]pyrrole, N-benzyl- H NMR, 4, 1041, 1042 lithiation, 4, 1051 UV spectra, 4, 1044 Thieno[3,2-6]pyrrole, 2,3-dihydro-desulfurization, 6, 984 oxidation, 6, 981... 

I) of which one form (picrate, m.p. 116°) is identical with dl-dihydro-de-N-methylheliotridane and the other (picrate, m.p. 126°) is diastereoisomeric with, and convertible into, it by, dehydrogenation to the corresponding pyrrole and hydrogenation of the latter in presence of copper chromite as catalyst. 

The importance of ring size holds also for tautomerism of -pyrrol-5-ones and. d -dihydro-6-pyridones. While the former compounds behave as cyclic 1-methyl-2-alkyl-2-hydroxy-5-pyrrolidones 179) (76) [or, on distillation, as the dehydrated l-methyl-2-alkyl-J -pyrrolones (77)], the latter compounds exist as acyclic N-methylamides of 8-oxo-acids (78) [as shown by infrared spectroscopy (/80)j. The dehydration of 78 during distillation to form l-methyl-2-alkyl-. -dihydro-6-pyridones (79) is achieved only with difficulty. 

Propionic acid, 2-iodo-3-nitro-, ethyl ester [Propanoic acid, 2-iodo-3-mtro-, ethyl ester], 65 2//-Pyran, 3,4-dihydro-, 51 2//-PYR AN-2-ONE, 49 2H Pyran 2-one, 5 bromo 5,6-dihydro, 50 27/-PYRAN-2-ONE, 5,6 DIHYDRO-, 49 PYRIDINE, 2,3,4,5 TETRAHYDRO, 118 Pyridines, -substituted, 34 a Pyrone-6-carboxyhc acid [2H Pyran-6-Larboxyhc acid 2-oxo ], 51 Pyrroles, 34... 

Ethoxypyrrolin-5-one l-Pyrrolin-5-one, 2-ethoxy- (8) 2H-Pyrrol-2-one, 5-ethoxy-3,4-dihydro- (9) (29473-56-1) tert-Butyl N-(l-ethoxycyclopropyl)carbamate Cyclopropanecar-bamic acid, 1-ethoxy-, tert-butyl ester (8) Carbamic acid, (1-ethoxycyclopropyl)-, 1,1-dimethylethyl ester (9) (28750-48-3 41879-49-6)... 

Alizadeh A, Rezvanian A, Zhu LG (2008) One-pot synthesis of 4,5-dihydro-lH-pyrrol-3-carboxamide derivatives via a four-component reaction. Tetrahedron 64 351-355... 

Nicht nur Pyrrole, 3-Amino-a-p5n one und 3-Hydroxyp Tidone, sondem auch a-P5Tidone selbst sind aus den Addukten von Butadien-carbon-saure-Derivaten zuganglich die Reduktion dieser Addukte mit Zink in Eisessig liefert bei 50—60°C durch Cyclisierung der intermediar auftre-tenden l-Aminobuten-(2)-ole-(4) 3-Hydroxy-3.6-dihydro-p5ridone-(2). 

Disubstituted thiophenes 96 and 1,2,5-tri- and 2,5-disubstituted pyrrole derivatives 97 are available readily from m-3,6-disubstituted-3,6-dihydro-l,2-dioxins in a one-pot synthesis. The reaction proceeds by an initial Kornblum-de la Mare rearrangement of the 3,6-dihydro-l,2-dioxin to its isomeric 1,4-diketone followed by the condensation with Lawesson s reagent, ammonium carbonate, or a primary amine (Scheme 21) <2002TL3199>. 

N-VINYLPYRROLIDIN-2-ONE AS A 3-AMINOPROPYL CARBANION EQUIVALENT IN THE SYNTHESIS OF SUBSTITUTED 1-PYRROLINES 2-PHENYL-1-PYRROLINE (2H-Pyrrole, 3,4-dihydro-5-phenyl-)... 

Although 2,5-dimethyl-1-hydroxypyrrole was synthesized in 1886 by Knorr, the parent 1-hydroxypyrrole was obtained only 90 years later. These compounds have not been widely investigated. The corresponding radicals, the pyrrole 1-oxyls, their 2,5-dihydro derivatives, and particularly the pyrrolidine 1-oxyls, if the adjacent positions to the nitrogen atom are substituted, can be stable. Many of these pyrrolidines have been prepared and used as spin labels. Only one 1-hydroxypyrrole, an antitumor antibiotic, has so far been isolated from living systems. 

In CHEC-II(1996), several applications of dihydro-2//-l,2,3-diazaphospholes, generated in situ from a ketone hydrazone and PC13, as useful intermediates for the synthesis of indoles, pyrroles, pyrrolylacetates, and 1,2-di-hydro-2-alkenyl-37/-pyrazol-3-ones are listed <1996CHEC-II(4)771>. 

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