329367-57-9Relevant 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 (2013/11/06)
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.
Synthesis of fused isoindoles via 1,3-dipolar cycloaddition of 1,3-oxazolium-5-olates (muenchnones) with nitro benzazoles
Pechenkin, Sergey Yu.,Starosotnikov, Aleksei M.,Bastrakov, Maxim A.,Kachala, Vadim V.,Shevelev, Svyatoslav A.
experimental part, p. 35 - 36 (2012/05/04)
1,3-Dipolar cycloaddition of 1,3-oxazolium-5-olates at benzazoles nitrated at the benzene ring affords the corresponding azoloisoindole derivatives.
Synthesis of 2-and 3-indolylpyrroles via 1,3-dipolar cycloadditions of muenchnones and nitroalkenes
Lopchuk, Justin M.,Gribble, Gordon W.
scheme or table, p. 1617 - 1631 (2011/05/04)
A series of 2-and 3-indolylpyrroles were generated via 1,3-dipolar cycloadditions between (2-nitrovinyl)indoles and symmetrical and unsymmetrical 1,3-oxazolium-5-olates (muenchnones). The Japan Institute of Heterocyclic Chemistry.
A convenient 1,3-dipolar cycloaddition approach to pyridylpyrroles
Lopchuk, Justin M.,Gribble, Gordon W.
scheme or table, p. 4106 - 4108 (2011/09/19)
A variety of 2-, 3-, and 4-pyridylpyrroles were synthesized in good to excellent yields via the 1,3-dipolar cycloaddition of symmetrical and unsymmetrical muenchnones and nitroalkenes. The unsymmetrical muenchnones show moderate to excellent regioselectiv
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.
