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Volumn 38, Issue 6, 1997, Pages 903-906

Novel tele nucleophilic aromatic substitutions in α-(benzotriazol-1-yl)alkyl aryl ketones

Author keywords

[No Author keywords available]

Indexed keywords

KETONE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS;

EID: 0031562022 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(96)02455-0 Document Type: Article

Times cited : (11)

References (23)

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18
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- 1-(diphenylmethyl)benzotriazole (1e) were prepared according to the literature procedures quoted. Compounds 1b and 1d were prepared by the following general procedure: phenyldichloromethane (for 1b) or (2-methylphenyl)phenylmethanol (for 1d) (30 mmol) with benzotriazole (40 mmol) in the presence of p-toluenesulfonic acid (0.3 g) in toluene (50 mL) was refluxed for 40 h. The mixture was washed with NaOH (aq. 2 N, 40 mL) and the organic layer was extracted with HCl (conc. 30 mL). The acid solution was neutralized with NaOH (aq. 4 N) to give a precipitate, which was washed with water (3 × 30 mL) and dried under vacuum to give the pure product (1b: 62%; 1d: 68%). New compounds 1b and 1d were characterized by NMR and CHN analyses. Compound 1c was prepared by the following procedure: to (4-methylbenzyl)benzotriazole (2.2 g, 10 mmol)
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20
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- 13C NMR spectroscopy and elemental analyses. Physical data for 2a (NMR, mp 265-267 °C) are consistent with the reported data (see: Katritzky, A. R.; Yang, Z.; Lam, J. N. Synthesis 1990, 666).
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- Katritzky, A.R.¹ Yang, Z.² Lam, J.N.³

21
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- 13C NMR spectroscopy and elemental analyses/HRMS
- 13C NMR spectroscopy and elemental analyses/HRMS.

22
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- For previously reported nucleophilic additions of organolithiums to an aromatic nucleus with a carbonyl group
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