- Aza-DielsAlder reaction between N-aryl-1-oxo-1H-isoindolium ions and tert-enamides: Steric effects on reaction outcome
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The synthesis of 5-substituted 6,6a-dihydroisoindolo[2,1-a]quinolin-11(5H)- ones via [4 + 2] imino-DielsAlder cyclization from N-aryl-3- hydroxyisoindolinones and N-vinyl lactams under Lewis acid-catalysed anhydrous conditions is reported. Reactions of N-(2-substituted-aryl)-3- hydroxyisoindolinones with N-vinylpyrrolidone under identical conditions resulted in the formation of 2-(2-substitued-aryl)-3-(2-(2-oxopyrrolidin-1-yl) vinyl)isoindolin-1-one analogues indicating steric hinderance as the cause of deviation. The probable mechanism of the reaction based on the results from X-ray crystallography and molecular modelling is discussed.
- Jha, Amitabh,Chou, Ting-Yi,ALJaroudi, Zainab,Ellis, Bobby D.,Cameron, T. Stanley
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supporting information
p. 848 - 857
(2014/05/06)
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- π-Stacked hydrogen-bonded dimers in 2-(2-nitrophenylaminocarbonyl)-benzoic acid, and hydrogen-bonded sheets in orthorhombic and monoclinic polymorphs of 2-(4-nitrophenylaminocarbonyl)benzoic acid
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Molecules of 2-(2-nitrophenylaminocarbonyl)benzoic acid, C 14H10N2O5, are linked into centrosymmetric R22(8) dimers by a single O-H...O hydrogen bond [H...O = 1.78 A, O...O = 2.623 (2) A and O-H...O = 178°] and these dimers are linked into sheets by a single aromatic π-π stacking interaction. The isomeric compound 2-(4-nitrophenylamino-carbonyl)benzoic acid crystallizes in two polymorphic forms. In the orthorhombic form (space group P21212 1 with Z′ = 1, crystallized from ethanol), the molecules are linked into sheets of R44(22) rings by a combination of one N-H...O hydrogen bond [H...O = 1.96 A, N...O = 2.833 (3) A and N-H...O = 171°] and one O-H...O hydrogen bond [H...O = 1.78 A, O...O = 2.614 (3) A and O-H...O = 173°]. In the monoclinic form (space group P21/n with Z′ = 2, crystallized from acetone), the molecules are linked by a combination of two N-H...O hydrogen bonds [H...O = 2.09 and 2.16 A, N...O = 2.873 (4) and 2.902 (3) A, and N-H...O = 147 and 141°] and two O-H...O hydrogen bonds [H...O = 1.84 and 1.83 A, O...O = 2.664 (3) and 2.666 (3) A, and O-H...O = 166 and 174°] into sheets of some complexity. These sheets are linked into a three-dimensional framework by a single C-H...O hydrogen bond [H...O = 2.45 A, C...O = 3.355 (4) A and C-H...O = 160°].
- Glidewell, Christopher,Low, John N.,Skakle, Janet M.S.,Wardell, James L.
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p. o120-o124
(2007/10/03)
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- Reaction of cyclic anhydrides with aromatic amines: Part I - Synthesis of anilinic acids from phthalic anhydride
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Some unreported anilinic acids 5a-j and 7 have been synthesised and their spectral data reported. Their in vitro insecticidal screening as protectants of maize (Zea mays) against Sitophilus zeamais shows 2-(N-naphthylcarbamoyl)benzoic acid 7 to be the most active member of the series.
- Omuaru, Victor O. T.,Boisa, N.,Obuzor, G. U.
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p. 704 - 706
(2007/10/03)
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