ChemInform Abstract: 4‐CARBOXY‐2,6‐DIARYLPYRIDINIUM DERIVATIVES

Katritzky, Alan R.; Cato, Stephen J.; Gabrielsen, B.; Patel, Ranjan C.

doi:10.1002/chin.198412216

Chemischer Informationsdienst

1984

DOI: 10.1002/chin.198412216

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ChemInform Abstract: 4‐CARBOXY‐2,6‐DIARYLPYRIDINIUM DERIVATIVES

Alan R. Katritzky¹,

Stephen J. Cato²,

B. Gabrielsen³

et al.

Abstract: Die Pyryliumsalze (III) reagieren mit den Aminen (IV) unter Bildung der Pyridiniumsalze (V).

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“…When 20a was dissolved in MeOH and the solution brought to pH 8, 23a was isolated. Compound 23a was reduced by NaBH4 to 24. Heating 16 or 15a + 16 at 180-200 °C gave 2,4-di-phenylpyrrole17 (27) (40%) and 1-phenyl-2-buten-l-one18 (28a) as proved by IR, NMR, and MS. If the crude pyrolysate was dissolved in CDC13 and the solution kept for 6-8 days 29a was formed.…”

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confidence: 87%

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Conversions of N-vinylpyridinium cations into tricyclic cage compounds

Katritzky¹,

Rubio²

1984

J. Org. Chem.

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residue which was chromatographed on a neutral alumina (activity I, CH2C12-AcOEt) column to afford the N-methyl derivative 19 (28 mg, 53%) which was identical with the sample obtained from 1 (IR and 'H NMR spectral comparison).ll-Cyan0-12-aza-l(2)-homodiamantane (22). A vigorously stirred mixture of azide 1 (225 mg, 0.98 mmol), NaCN (5 g, 102 mmol), and Adogen 464 (0.3 mL) in water (60 mL) and n-hexane (200 mL) was irradiated as above for 3.5 h. The workup and chromatography on a silica gel column (CH2C12-AcOEt) afforded the amino nitrile 22 as colorless crystals: 96 mg (43%); mp 186-188 "C; IR (KBr) 3355,2920,2230,1437,1138 cm-' ; 'H NMR (CDClJ 6 3.3-3.0 (m, l), 1.98 ( 8 , 1, D20 exchangeable), 2.5-1.3 (m, 18); mass spectrum, m / e (relative intensity) 228 (M+, loo), 227 (38).

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confidence: 87%

“…Treatment of the crude 20b with base (0.1 M NaOH) gave 23b. Pyrolysis of 15b at 180-190 °C gave 29b and 2,4-diphenylpyrrole (27) (Scheme II).…”

mentioning

confidence: 99%

Conversions of N-vinylpyridinium cations into tricyclic cage compounds

Katritzky¹,

Rubio²

1984

J. Org. Chem.

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ChemInform Abstract: 4‐CARBOXY‐2,6‐DIARYLPYRIDINIUM DERIVATIVES

Abstract: Die Pyryliumsalze (III) reagieren mit den Aminen (IV) unter Bildung der Pyridiniumsalze (V).

Cited by 1 publication

References 0 publications

Conversions of N-vinylpyridinium cations into tricyclic cage compounds

Conversions of N-vinylpyridinium cations into tricyclic cage compounds

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