67067-96-3Relevant academic research and scientific papers
Synthesis of Heteroaryl-Substituted Pyrroles via the 1,3-Dipolar Cycloaddition of Unsymmetrical Münchnones and Nitrovinylheterocycles
Lopchuk, Justin M.,Song, Mia,Butler, Blythe,Gribble, Gordon W.
, p. 2776 - 2780 (2015/09/15)
A series of furanyl-, thiophenyl-, and pyrrolo-substituted pyrroles were prepared via the 1,3-dipolar cycloaddition of unsymmetrical münchnones and nitrovinylheterocycles. The regiochemical outcome of the furan and thiophene cycloadditions compares favorably to previously reported cycloadditions with β-nitrostyrene, while the nitrovinylpyrrole cycloadditions mirror the results observed with nitrovinylindole.
Rhodium-catalyzed intermolecular reaction of alkyl azides with diazo(aryl)acetates
Gu, Peiming,Wu, Xiu-Ping,Su, Yan,Li, Xue-Qiang,Xue, Ping,Li, Rui
, p. 535 - 538 (2014/03/21)
An efficient intermolecular interception of alkyl azides by diazo(aryl)acetates was achieved in the presence of dirhodium tetraoctanoate. The initial products were unstable α-imino esters, and overaddition of carbenoids to the C-N double bonds was avoided. After acidic workup, the corresponding α-keto esters were obtained in good to excellent yields. Georg Thieme Verlag Stuttgart New York.
What controls regiochemistry in 1,3-dipolar cycloadditions of Muenchnones with nitrostyrenes?
Lopchuk, Justin M.,Hughes, Russell P.,Gribble, Gordon W.
supporting information, p. 5218 - 5221 (2013/11/06)
The distinct experimentally observed regiochemistries of the reactions between mesoionic muenchnones and β-nitrostyrenes or phenylacetylene are shown by DFT/BDA/ETS-NOCV analyses of the transition states to be dominated by steric and reactant reorganization factors, rather than the orbital overlap considerations predicted by Frontier Molecular Orbital (FMO) Theory.
Ruthenium-catalyzed one-pot carbenoid N-H insertion reactions and diastereoselective synthesis of prolines
Deng, Qing-Hai,Xu, Hai-Wei,Yuen, Angella Wing-Hoi,Xu, Zhen-Jiang,Che, Chi-Ming
supporting information; experimental part, p. 1529 - 1532 (2009/04/07)
Aryl- and aliphatic-substituted 3-hydroxyprolines and various other amino esters are conveniently prepared by [RuCI2(p-cymene)] 2-catalyzed one-pot intramolecular and intermolecular carbenoid N-H insertion reactions, respectively, and the prolines are formed with high diastereoselectivities. The catalytic reactions are tolerant toward air/moisture, and the product yields are insensitive to the organic solvents used.
New method for the synthesis of 2-phenylproline and its derivatives
Martirosyan,Gasparyan,Oganesyan,Mndzhoyan,Aleksanyan,Nikishchenko,Babayan
, p. 416 - 420 (2007/10/03)
A new method has been developed for the synthesis of 2-phenylproline and its derivatives by intramolecular cyclization of the corresponding derivatives of N-(3-chloro- or 1-oxo-3-chloropropyl)-α-phenylglycine under phase transfer catalysis conditions.
Regioselective 1,3-dipolar cycloaddition reactions of unsymmetrical munchnones (1,3-oxazolium-5-olates) with 2- and 3-nitroindoles. A new synthesis of pyrrolo[3,4-b]indoles
Gribble, Gordon W.,Pelkey, Erin T.,Simon, Wendy M.,Trujillo, Hernando A.
, p. 10133 - 10140 (2007/10/03)
The unsymmetrical mesoionic munchnones 13 (3-benzyl-2-methyl-4-phenyl-1,3-oxazolium-5-olate) and 14 (3-benzyl-4-methyl-2-phenyl-1,3-oxazolium-5-olate) react with the N-protected 2- and 3-nitroindoles 1 (ethyl 2-nitroindole-1-carboxylate), 6 (3-nitro-1-(phenylsulfonyl)indole), and 17 (ethyl 3-nitroindole-carboxylate) in refluxing THF to afford in good to excellent yields the pyrrolo[3,4-b]indoles 15 (2-benzyl-1-methyl-3-phenyl-4-carboethoxy-2,4-dihydropyrrolo[3,4-b]indole), 16 (2-benzyl-3-methyl-1-phenyl-4-carboethoxy-2,4-dihydropyrrolo[3,4-b]indole), 18 (2-benzylmethyl-3-phenyl-4-(phenylsulfonyl)-2,4-dihydropyrrolo[3,4-b]indole), and 19 (2-benzyl-3-methyl-1-phenyl-4-(phenylsulfonyl)-2,4-dihydropyrrolo[3,4-b]indol e). In several cases the regiochemistry, which is opposite to that predicted by FMO theory, is very high and leads essentially to a single pyrrolo[3,4-b]indole; e.g., 6+ 13→19 in 74% yield. (C) 2000 Elsevier Science Ltd.
Tandem 1,3-dipolar cycloadditions of muenchnones. Syntheses and molecular structures of 10-azatetracyclo[6.3.0.04,11.05,9]undecanes and azahomopentaprismane
Gribble, Gordon W.,Sponholtz III, William R.,Switzer, Frank L.,D'Amato, Ferdinando J.,Byrn, Marianne P.
, p. 993 - 994 (2007/10/03)
Photocyclization of 10-benzyl-9,11-diphenyl-10-azatetracyclo[6.3.0.04,11.0 5,9]undeca-2,6-diene 11, prepared in one step from muenchnone 7 and cycloocta-1,3,5,7-tetraene 10, gives azahomopentaprismane 12.
Phosphatase inhibitors. III. Benzylaminophosphonic acids as potent inhibitors of human prostatic acid phosphatase
Beers, Scott A.,Schwender, Charles F.,Loughney, Deborah A.,Malloy, Elizabeth,Demarest, Keith,Jordan, Jerold
, p. 1693 - 1701 (2007/10/03)
Further investigation of the structural requirements of a series of benzylphosphonic acid inhibitors of human prostatic acid phosphatase has led to the highly potent series of α-aminobenzylphosphonic acids. The α-benzylaminobenzylphosphonic acid, with an IC50 = 4 nM, exhibited a 3500-fold improvement in potency over the carbon analogue, α-phenylethyl. The enhanced potency may be due to a combination of four favorable interactions including those with the phosphate binding region, the presence the hydrophobic moieties of the benzylamino and phenylphosphonic acid, and a rigid conformer produced by an internal salt bridge between the phosphonate and the α-amino group. Replacement of the phosphonic acid moiety with a phosphinic or carboxylic acid as well as deletion of the benzyl substitution on the α-amino group led to great reductions in potency.
