668988-46-3Relevant academic research and scientific papers
What controls regiochemistry in 1,3-dipolar cycloadditions of Muenchnones with nitrostyrenes?
Lopchuk, Justin M.,Hughes, Russell P.,Gribble, Gordon W.
, p. 5218 - 5221 (2013)
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.
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.
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.
