Cyclizations of Dialdehydes with Nitromethane. XII.<sup>1</sup> o-Phthalaldehyde<sup>2</sup>

Baer, Hans H.; Achmatowicz, Barbara

doi:10.1021/jo01034a014

Cited by 19 publications

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“…Synthesis of 4-hydroxy-3,4-dihydro-2-(JH)-isoquinoline carboxamidine sulphate (4-hydroxydebrisoquine sulphate) 2-(1 '-Hydroxy-2'-nitroethyl)-benzaldehyde lactol (2.93 g; m.p. 120-1220C dec.) was first synthesized by the method of Baer & Achmatowicz (1964). A solution of the lactol (1.0 g) in 50% acetic acid (10 ml) was then hydrogenated for 2-3 h according to Nakao, Yura & Ito (1966) in the presence of platinum dioxide (40 mg) at a pressure of 280 kPa.…”

Section: Methodsmentioning

confidence: 99%

“…Ammonium bromide precipitated and the mixture was then left overnight at 0°C to complete the reaction. Baer & Achmatowicz (1964). A solution of the lactol (1.0 g) in 50% acetic acid (10 ml) was then hydrogenated for 2-3 h according to Nakao, Yura & Ito (1966) in the presence of platinum dioxide (40 mg) at a pressure of 280 kPa.…”

Section: Synthesis Of 34-dihydro-2-(jh)-isoquinoline [14c]-carboxamimentioning

confidence: 99%

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The metabolism of [14C]‐debrisoquine in man.

Idle¹,

Mahgoub²,

Angelo³

et al. 1979

Brit J Clinical Pharma

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I The synthesis of ['4C]-debrisoquine hydrochloride and 4-hydroxy-debrisoquine sulphate is described. 2 The metabolic fate and excretion profile in both urine and faeces of "4C-labelled debrisoquine was studied in five healthy human subjects. 3 Investigations showed that the drug is well-absorbed after a single oral dose of 32 mg and quantitatively eliminated from the body within three days. 4 4-Hydroxy-debrisoquine is the major metabolite of debrisoquine, although significant amounts of 5-,6-, 7-and 8-hydroxy-debrisoquine are also formed. S Electron-capture gas chromatography is a useful method for measuring debrisoquine and its five hydroxylated metabolites in urine at the pg level.

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Section: Methodsmentioning

confidence: 99%

Section: Synthesis Of 34-dihydro-2-(jh)-isoquinoline [14c]-carboxamimentioning

confidence: 99%

The metabolism of [14C]‐debrisoquine in man.

Idle¹,

Mahgoub²,

Angelo³

et al. 1979

Brit J Clinical Pharma

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“…As described for succinaldehyde (8), NaOH did not induce the reaction of phthalaldehyde with nitromethane. Therefore, the weak base Bu 4 NF was used as reported in the literature [17,22], which provided the nitrodiol 11 [23] in 55% yield. Reduction of the nitro moiety with H 2 and Raney-Ni afforded the aminodiol 12 [24], which was acylated to give the amide 13 (Scheme 3).…”

Section: Resultsmentioning

confidence: 99%

Diastereoselective Synthesis of Cyclic Five‐Membered trans,trans‐Configured Nitrodiols by Double Henry Reaction of 1,4‐Dialdehydes

Fröhlich

Lehmkuhl

Fröhlich

et al. 2015

Archiv der Pharmazie

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Conformationally constrained perhydroquinoxalines 4 show high κ receptor affinity, selectivity over related receptors and full agonistic activity. Since the κ affinity can be correlated with the dihedral angle of the ethylenediamine pharmacophore (4a: 55°/71°), the dihedral angles of the postulated cyclopentane derivative 5a (73°/84°) and indane derivative 6a (77°/81°) were calculated. The first step of the synthesis represents a double Henry reaction of 1,4-dialdehydes 8 and 10 with nitromethane, leading predominantly to the trans,trans-configured nitrodiols 9 and 11. X-ray crystal structure analyses of 9 and 11 led to dihedral angles O2 N−C−C−OH of 73.4 and 88.3°, respectively, which reflect the calculated dihedral angles of the hypothesized final products 5a and 6a.

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“…Condensation reactions which were studied include o-phthaldehyde with nitromethane in basic methanol (19) benzoylacetone with the ionic and neutral forms of glyoxylic acid (241), and the aldol condensation of n-butyraldehyde (322). The latter w7as followed by measuring the decrease in its ultraviolet spectra with time.…”

Section: Reaction Mechanismsmentioning

confidence: 99%

Ultraviolet Spectrometry

Crummett¹

1966

Anal. Chem.

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A chapter by Ferguson (122) in "Advances in Analytical Chemistry and Instrumentation," Vol. 4 and one by Schilt and Jaselskis (338) in "Treatise on Analytical Chemistry" Part I, Vol. 5, covers the fundamentals."Interpretation of the Ultraviolet Spectra of Natural Products" by Scott (341) presents "available correlative data, model systems, and working rules" to aid the chemist in interpreting spectra.Single chromophores, conjugated chromophores, C-aromatic compounds, O-and S-heteroaromatic compounds, and Nheteroaromatic compounds are treated in this way.

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Cyclizations of Dialdehydes with Nitromethane. XII.¹ o-Phthalaldehyde²

Cited by 19 publications

References 0 publications

The metabolism of [14C]‐debrisoquine in man.

The metabolism of [14C]‐debrisoquine in man.

Diastereoselective Synthesis of Cyclic Five‐Membered trans,trans‐Configured Nitrodiols by Double Henry Reaction of 1,4‐Dialdehydes

Ultraviolet Spectrometry

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Cyclizations of Dialdehydes with Nitromethane. XII.1 o-Phthalaldehyde2

Cited by 19 publications

References 0 publications

The metabolism of [14C]‐debrisoquine in man.

The metabolism of [14C]‐debrisoquine in man.

Diastereoselective Synthesis of Cyclic Five‐Membered trans,trans‐Configured Nitrodiols by Double Henry Reaction of 1,4‐Dialdehydes

Ultraviolet Spectrometry

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Cyclizations of Dialdehydes with Nitromethane. XII.¹ o-Phthalaldehyde²