Reactions of Phthalaldehydic Acid

Wheeler, D. D.; Young, Douglas L.; Erley, D. S.

doi:10.1021/jo01356a022

Cited by 62 publications

(38 citation statements)

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“…77.40 (7) -44.3 (3) In spite of the presence of the tert butyl substituents, the hydroxy groups in both structures are involved in the in this region being doubled and broadened. The absence of signals at δ 6.0-6.3 in the spectra of both compounds suggests that indole is attached at position 3, although other directions of the amidomethylation of indoles in strongly acidic media were also described in the litera ture.…”

Section: Methodsmentioning

confidence: 99%

2-Aminothiophene derivatives in a novel synthesis of phthalimidines

et al. 2011

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New aminophthalides were synthesized from o formylbenzoic acid and substituted 2 ami nothiophenes. Two of these compounds underwent recyclization in boiling Ac 2 O to give the previously unknown 3 acetoxy 2 (3 cyano 4,5 dimethylthiophen 2 yl) 1,3 dihydroisoindol 1 one and 3 acetoxy 2 (3 cyano 4,5 tetramethylenethiophen 2 yl) 1,3 dihydroisoindol 1 one. The possible reaction mechanism and factors preventing the recyclization, in particular, the formation of intramolecular hydrogen bonds in the starting phthalides, were discussed. Some reactions of the resulting compounds with C nucleophiles in trifluoroacetic acid were investigated. Two derivatives containing 4 hydroxy 3,5 di tert butylphenyl substituents were studied by X ray diffraction.Key words: o formylbenzoic acid, 2 aminothiophenes, 3 hetarylaminophthalides, azome thines of o formylbenzoic acid, acetic anhydride, 2 hetaryl 3 acyloxyphthalimidines, 2,6 di tert butylphenol, indole, X ray diffraction study.Recently, we have reported on the new synthesis of phthalimidines by the recyclization of arylaminophthal ides or acyl hydrazones of o formylbenzoic acid (1) in acetic anhydride. 1 The resulting phthalimidines were used in the synthesis of potentially biologically active phthal imidines attached via an amide bridged to quinoline de rivatives. 2 The aim of the present study was to extend the recycl ization of arylaminophthalides of o formylbenzoic acid to the synthesis of phthalimidines containing thiophene sub stituents at position 2. It was found that tautomeric o formylbenzoic acid (1), which reacts with primary aromatic amines to give 3 arylaminophthalides, 1,3 reacts in a similar way with 2 aminothiophene derivatives 2 (Scheme 1).However, the resulting hetarylaminophthalides 3a-c sharply differ in the chemical properties. Compounds con taining the cyano group 3a,b easily undergo recyclization in refluxing acetic anhydride to give the corresponding phthalimidines 4a,b (see Scheme 1), as has been described for arylaminophthalides, 1 whereas compound 3c contain ing the ethoxycarbonyl group in the ortho position with respect to the amino group is not involved in this reaction. This behavior can be attributed to both the steric and elec tronic factors. However, the experimental data obtained Scheme 1 R 1 = CN, R 2 = R 3 = Me (a); R 1 = CN, R 2 + R 3 = (CH 2 ) 4 (b); R 1 = COOEt, R 2 = H, R 3 = Et (c)

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Section: Methodsmentioning

confidence: 99%

2-Aminothiophene derivatives in a novel synthesis of phthalimidines

et al. 2011

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“…Steric models show [61] that the open tautomers (lOA) can exist only in a non-planar conformation, which inhibits the conjugation ofC=O and COOH groups with the benzene ring. 2-Formylbenzoic acid in the solid state exists as the cyclic hydroxyphthalide (lOB, R = H) [62][63][64], and this form also predominates in the solutions (see Table 3) [5,8,12,26,65]. The same behavior applies to solutions of 2-formyl-5,6-dimethoxybenzoic (opianic) acid [16,18], but for 2-formyl-3-hydroxy-2-methylpyridine-4-carboxylic acid the equilibrium is shifted toward the open form [14,18].…”

Section: -Acylpropionic Acids and Substitutedmentioning

confidence: 99%

Intramolecular Reversible Addition Reactions to the C=O Group

Valters¹,

Flitsch

1985

Ring-Chain Tautomerism

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“…6, 8 Phthalides are easily identified due to intense absorption bands of the carbonyl groups (1715-1750 cm -1 ), antisymmetric (1050-1096 cm -1 ) and symmetric (847-900 cm -1 ) С-О-С vibrations in the IR spectra. 6 At the same time, reaction of о formylbenzoic acid with of anthranilohydrazide affords normal hydrazone, i.e., derivative of the open tautomeric form 1а (see Ref. 9).…”

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A new synthesis of phthalimidines

et al. 2009

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A new synthesis of phthalimidines is described. 3 Acyloxy 2 aryl and 2 acylamino 3 acyloxyphthalimidines were prepared by the reaction of 3 arylaminophthalides or o formylbenzoic acid acylhydrazones with acetic or propionic anhydrides. Their reactions with O , N , S , and C nucleophiles were studied. The structure of 2 acetyl(cyanoacetyl)amino 3 acetoxyindolin 1 one was confirmed by X ray diffraction analysis.Key words: о formylbenzoic acid, 3 arylaminophthalides, o formylbenzoic acid acyl hydrazones, acetic and propionic anhydrides, 3 acyloxy 2 aryl phthalimidines, 2 acyl amino 3 acyloxyphthalimidines, X ray diffraction analysis.

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Reactions of Phthalaldehydic Acid

Cited by 62 publications

References 0 publications

2-Aminothiophene derivatives in a novel synthesis of phthalimidines

2-Aminothiophene derivatives in a novel synthesis of phthalimidines

Intramolecular Reversible Addition Reactions to the C=O Group

A new synthesis of phthalimidines

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