24413-66-9Relevant academic research and scientific papers
On the anomalous behaviour of certain 1-(4-methoxyphenyl)azetidin-2-ones towards cerium(IV) ammonium nitrate (CAN). Structure-reactivity studies
Sapi, Attila,Bertha, Ferenc,Fetter, Jozsef,Kajtar-Peredy, Maria,Keseru, Gyoergy M.,Lempert, Karoly
, p. 771 - 782 (1996)
On treatment with CAN, acetylthiazolidinylazetidin-2-one 12 undergoes ring transformation to afford compound 22, similarly to azetidin-2-ones 2a and 2b studied earlier (all with like configurations at C-4 and C-2'). In contrast, acetylthiazolidinylazetidin-2-one 11 is N-demethoxy-phenylated under the same conditions, similarly to azetidin-2-ones 1a and 1b studied earlier (all with unlike configurations at C-4 and C-2'). Both epimers, with like as well as unlike configurations at C-4 and C-2'. of acetyloxazolidinyl derivative 7 are N-demethoxyphenylated by CAN. These observations support the mechanism, suggested earlier for the CAN induced novel ring transformation reaction.
Catalyst-Free Synthesis of Aryl Diamines via a Three-Step Reaction Process
Bulut, Safak,Queen, Wendy L.
, p. 3806 - 3818 (2018/04/14)
The formation of C-N bonds with aryl amines is one of the most widely studied reactions in organic chemistry. Despite this, it is still highly challenging, often requiring expensive, precious metal-based catalysts. Here we report an easy catalyst-free methodology for constructing C-N bonds. The method, which proceeds via the in situ formation of closed ring amidinium ions, allows the preparation of a series of symmetrical and/or unsymmetrical aryl diamines in notably high yields (82-98%) and purity and with a variety of different substituents. The methodology is shown successful for the preparation of aryl diamines having para- and/or meta-substituted carboxyl, nitro, bromo, methoxy, or methyl groups. This green synthetic pathway, which is catalyst free, requires only three steps, and proceeds without the need for purification. Further, it is a new sustainable, economically viable method to achieve an otherwise challenging bond formation.
A silver complex of N,N′-disubstituted cyclic thiourea as an anti-inflammatory inhibitor of IκB kinase
Lin, Iris Wing-Shan,Lok, Chun-Nam,Yan, Kun,Che, Chi-Ming
supporting information, p. 3297 - 3299 (2013/06/27)
A silver complex of N,N′-disubstituted cyclic thiourea inhibits inflammatory cytokine-stimulated NF-κB activity via IκB kinase inactivation. The Royal Society of Chemistry 2013.
PKas of the conjugate acids of N-heterocyclic carbenes in water
Higgins, Eleanor M.,Sherwood, Jennifer A.,Lindsay, Anita G.,Armstrong, James,Massey, Richard S.,Alder, Roger W.,O'Donoghue, Annmarie C.
supporting information; experimental part, p. 1559 - 1561 (2011/03/22)
pKa values of 19.8-28.2 are reported for the conjugate acids of a large series of NHCs in water. The effects of ring size, N-substituent and C(4)-C(5) saturation on pKa are discussed.
Thiadiazolidine 1-oxide systems for phosphine-free palladium-mediated catalysis
Buckley, Benjamin R.,Neary, Stephen P.
experimental part, p. 7988 - 7994 (2010/10/21)
We herein report several highly active catalyst systems with thiadiazolidine 1-oxides as ligands for palladium in the Mizoroki-Heck reaction. Excellent yields of stilbenes derived from aryl iodides and bromides have been achieved using as little as 0.00002 mol % catalyst. The ligand/palladium system can be stored as a stock solution open to air at room temperature with no observable loss of activity for a period of several months.
N-Heterocyclic phosphenium cations: Syntheses and cycloaddition reactions
Caputo, Christine A.,Price, Jacquelyn T.,Jennings, Michael C.,McDonald, Robert,Jones, Nathan D.
, p. 3461 - 3469 (2008/09/21)
A series of trifluoromethanesulfonate (OTf) salts of N-heterocyclic phospheniums (NHP) bearing phenyl (1a), para-methoxyphenyl (1b), 2,6-diisopropylphenyl (1c) and mesityl (1d) substituents is reported. The compounds 1b-d are made by a modification to a literature procedure that improves the overall yields for 1c and 1d by 15 and 23%, respectively. Two unwanted side-products in the synthesis of 1d, the diammonium salt, [(2,6-iPr-C6H3)N(H)2CH2CH 2N(H)2(2,6-iPr-C6H3)]Cl2 (4) and the bisphosphine (2,6-iPr-C6H3)N(PCl 2)CH2CH2N(PCl2)(2,6-iPr-C 6H3) (5), are crystallographically characterized, as is the intermediate cyclic chlorophosphine, C1PN(4-OMe-C6H 4)CH2CH2N(4-OMe-C6H4) (3b). The phenyl-substituted NHP 1a is fully characterized, including by X-ray crystallography, for the first time; this compound contains a short P-O contact of 2.1850(14) A Cycloaddition reactions of 1a-d with 2,3-dimethyl-1,3- butadiene give the expected spirocyclic phospholeniums, 7,8-dimethyl-1,4-diaryl- 1,4-diaza-5-phopshoniaspiro[4.4]non-7-ene, as their OTf salts (6a-d), while reactions with N,N′-dimesityl-1,4-diaza-1,3-butadiene give, except in the case of 1c, which is too bulky to react, the aza analogues, 1,4-dimesityl-6,9- diaryl-1,4,6,9-tetraaza-5-phosphoniaspiro[4.4]non-2-ene (7a, 7b and 7d). The sterically congested 7d is in thermal equilibrium with 1d and free diazadiene, and undergoes a substitution reaction with 2,3-dimethyl-1,3-butadiene to give 6d.
