168399-08-4Relevant articles and documents
Bicyclic-Fused Heteroaryl or Aryl Compounds
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Paragraph 0753, (2015/10/28)
Compounds, tautomers and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula Ia, as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.
Synthesis of imidazolidin-2-one-4-carboxylate and of (tetrahydro)pyrimidin- 2-one-5-carboxylate via an efficient modification of the Hofmann rearrangement
Angelici, Gaetano,Contaldi, Simone,Lynn Green, Sarah,Tomasini, Claudia
experimental part, p. 1849 - 1852 (2008/10/09)
A mild and efficient methodology for the rearrangement of protected asparagine and protected glutamine is reported; good results are obtained with a wide selection of protecting groups. The Royal Society of Chemistry.
IMIDAZOLIDINE CARBOXAMIDE DERIVATIVES AS P2X7 MODULATORS
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Page/Page column 37, (2008/12/04)
The present invention relates to a compound of Formula (I) or a pharmaceutically acceptable salt thereof: The compounds or salts modulate P2X7 receptor function and are capable of antagonizing the effects of ATP at the P2X7 receptor (P2X7 receptor antagonists). The invention also provides the use of such compounds or salts, or pharmaceutical compositions thereof, in the treatment or prevention of disorders / diseases mediated by the P2X7 receptor, for example pain, inflammation or a neurodegenerative disease, in particular pain such as inflammatory pain, neuropathic pain or visceral pain.
Synthesis of dirhodium(II) tetrakis[methyl 1-(3-phenylpropanoyl)-2- oxaimidazolidine-4(S)-carboxylate], Rh2(4S-MPPIM)4
Doyle, Michael P.,Colyer, John T.
, p. 3601 - 3604 (2007/10/03)
The large-scale synthesis with greatly improved yields of methyl 1-(3-phenylpropanoyl)-2-oxaimidazolidine-4(S)-carboxylate and the chiral dirhodium(II) carboxamidate derived from it, Rh2(4S-MPPIM) 4, is described. The key step in the
First attempts at differential diastereoselection in catalytic reactions of N-chirally substituted dirhodium(II) tetrakis[methyl 2-oxoimidazolidine-4(S)-carboxylates] with diazoacetates
Doyle,Timmons,Arndt,Duursma,Colyer,Bruenner
, p. 2156 - 2161 (2007/10/03)
Chiral attachments on 2-oxoimidazolidine-4(S)-carboxylate ligands for dirhodium(II) can provide differential diastereoselection in catalytic reactions of diazo compounds. The synthesis of these heterocyclic ligands from the readily available amino acid as
Enantioselective intramolecular cyclopropanations of allylic and homoallylic diazoacetates and diazoacetamides using chiral dirhodium(II) carboxamide catalysts
Doyle, Michael P.,Austin, Richard E.,Bailey, A. Scott,Dwyer, Michael P.,Dyatkin, Alexey B.,Kalinin, Alexey V.,Kwan, Michelle M. Y.,Liras, Spiros,Oalmann, Christopher J.,Pieters, Roland J.,Protopopova, Marina N.,Raab, Conrad E.,Roos, Gregory H. P.,Zhou, Qi-Lin,Martin, Stephen F.
, p. 5763 - 5775 (2007/10/02)
Diazo decomposition of allylic and homoallylic diazoacetates 10a-p and 22a-j catalyzed by chiral dirhodium(II) tetrakis[methyl 2-pyrrolidone-5(S)-carboxylate], Rh2(SS-MEPY)4 (7), and its enantiomer, Rh2(5R-MEPY)4 (8), produces the corresponding intramolecular cyclopropanation products 11a-p and 23a-j in good to excellent yields and with exceptional enantioselectivity. Higher enantiocontrol is observed with allylic diazoacetates than with their homoallylic counterparts, but allylic diazoacetates are subject to greater variations in enantioselectivities with changes in substitution patterns on the carbon-carbon double bond. For example, the enantioselectivities in the intramolecular cyclopropanations of 3-alkyl/aryl-2(Z)-alken-1-yl diazoacetates are generally ≥94%, whereas the cyclizations of the homologous 4-alkyl/aryl-3(Z)-alken-1-yl diazoacetates are typically in the range of 70-90% ee. The corresponding 3-alkyl/aryl-2(E)-alken-1-yl and 4-alkyl/aryl-3(E)-alken-1-yl diazoacetates undergo cyclization with slightly lower ee's (54-85%). Although the Rh2(5S-MEPY)4-catalyzed cyclization of the 2-methallyl diazoacetate 10c proceeds with only 7% ee, alternative chiral dirhodium(II) catalysts, including those with methyl N-acylimidazolidin-2-one-4(5)-carboxylate ligands such as Rh2(4S-MACIM)4 (14) and Rh2(4S-MPAIM)4 (15), may be employed to increase the level of enantiocontrol to 78 and 65%, respectively. Some allylic diazoacetamides also undergo highly enantioselective cyclization to form cyclopropyl lactams as illustrated by the diazo decomposition of N-allyl diazoacetamide (19) in the presence of dirhodium(II) tetrakis[methyl 2-oxazolidinone-4(S)-carboxylate], Rh2(4S-MEOX)4, to give the 3-azabicyclo[3.1.0]hexan-2-one 20 in 98% ee. The absolute configuration and the level of enantiocontrol in these intramolecular cyclopropanations have been interpreted by a transition state model in which the important determinants are (i) the preferred conformation about the rhodium-carbon bond; (ii) the trajectory of approach of the double bond to the metallocarbene center; and (iii) the orientation of the double bond with respect to the chiral face of the catalyst.
Stereospecific Amination by Dynamic Kinetic Resolution Utilizing 2-Oxoimidazolidine-4-carboxylate as a Novel Chiral Auxiliary
Kubota, Hitoshi,Kubo, Akira,Takahashi, Masami,Shimizu, Ryo,Da-te, Tadamasa,et al.
, p. 6776 - 6784 (2007/10/03)
A novel type of stereospecific amination by dynamic kinetic resolution using (4S)-2-oxoimidazolidine-4-carboxylate (1) as a chiral auxiliary was developed. A reaction of a diastereomeric mixture of (4S)-3--2-oxoimidazolidine-4-carboxylates 4 with an amine in the presence of a base in HMPA predominantly afforded (4S)-3--2-oxoimidazolidine-4-carboxylates (S,R)-7 in good yields.The reaction proceeded by stereospecific SN2 type amination incorporated with rapid interconversion between the substrates (S,S)-4 and (S,R)-4.Mechanistic study suggested that the unique stereoselectivity was induced through the interaction between an amine and the ester group of (S,S)-4 in the transition state.The chiral auxiliary was easily removed with alkoxide anion to afford the α-amino acid synthon in good yields.
