A CONDENSATION OF ACETOPHENONE WITH ISATIN BY THE KNOEVENAGEL METHOD<sup>1</sup>

Lindwall, H. G.; Maclennan, J. S.

doi:10.1021/ja01351a034

Cited by 75 publications

(20 citation statements)

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“…The chalcones 1a-e were prepared by the reaction of indenoquinoxaline with acetophenones in a solvent free condition catalyzed by dimethylamine and then glacial acetic acid and HCl. 10,14 These chalcones reacted with hydrazine hydrate in toluene and then in situ with lead(IV) acetate (LTA or Pb(OAc) 4 ) to afford new spiro indenoquinoxaline-cyclopropane derivatives 2a-e and 3a-e (Scheme 3).…”

Section: Resultsmentioning

confidence: 99%

One-pot diastereoselective synthesis of new spiro indenoquinoxaline derivatives containing cyclopropane ring

Shaabanzadeh¹,

Khabari²

2009

Arkivoc

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Section: Resultsmentioning

confidence: 99%

One-pot diastereoselective synthesis of new spiro indenoquinoxaline derivatives containing cyclopropane ring

Shaabanzadeh¹,

Khabari²

2009

Arkivoc

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“…Analyses: for (I), yield 40%, m.p. 423-425 K (decomposition) (literature value 442-445 K; Lindwall & Maclennan, 1932) A stereoview of part of the crystal structure of (XI) (CSD refcode TEQVUH; Luppi et al, 2006), showing the formation of a hydrogenbonded chain of edge-fused R 2 2 (9) rings along [100]. Hydrogen bonds are shown as dashed lines.…”

Section: Methodsmentioning

confidence: 99%

Hydrogen-bonding patterns in 3-alkyl-3-hydroxyindolin-2-ones

et al. 2010

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The molecules of racemic 3-benzoylmethyl-3-hydroxyindolin-2-one, C(16)H(13)NO(3), (I), are linked by a combination of N-H...O and O-H...O hydrogen bonds into a chain of centrosymmetric edge-fused R(2)(2)(10) and R(4)(4)(12) rings. Five monosubstituted analogues of (I), namely racemic 3-hydroxy-3-[(4-methylbenzoyl)methyl]indolin-2-one, C(17)H(15)NO(3), (II), racemic 3-[(4-fluorobenzoyl)methyl]-3-hydroxyindolin-2-one, C(16)H(12)FNO(3), (III), racemic 3-[(4-chlorobenzoyl)methyl]-3-hydroxyindolin-2-one, C(16)H(12)ClNO(3), (IV), racemic 3-[(4-bromobenzoyl)methyl]-3-hydroxyindolin-2-one, C(16)H(12)BrNO(3), (V), and racemic 3-hydroxy-3-[(4-nitrobenzoyl)methyl]indolin-2-one, C(16)H(12)N(2)O(5), (VI), are isomorphous in space group P-1. In each of compounds (II)-(VI), a combination of N-H...O and O-H...O hydrogen bonds generates a chain of centrosymmetric edge-fused R(2)(2)(8) and R(2)(2)(10) rings, and these chains are linked into sheets by an aromatic pi-pi stacking interaction. No two of the structures of (II)-(VI) exhibit the same combination of weak hydrogen bonds of C-H...O and C-H...pi(arene) types. The molecules of racemic 3-hydroxy-3-(2-thienylcarbonylmethyl)indolin-2-one, C(14)H(11)NO(3)S, (VII), form hydrogen-bonded chains very similar to those in (II)-(VI), but here the sheet formation depends upon a weak pi-pi stacking interaction between thienyl rings. Comparisons are drawn between the crystal structures of compounds (I)-(VII) and those of some recently reported analogues having no aromatic group in the side chain.

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“…The compounds were prepared in a way similar to that described earliery by Lindwall and McLennan [17]. Equimolecular proportions (0.05 mol) of isatin, acetophenone and/or its para (methyl-, ethyl-, methoxy-, chloro-and bromo-)derivatives were dissolved in ethanol (100 ml), to which ammonium hydroxide (2 ml/g istain) was added and the reaction mixture was set aside over night at room temperature.…”

Section: Preparation Of 3-acylidene Oxindole (2a-h)mentioning

confidence: 99%