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Volumn 41, Issue 11, 2000, Pages 1845-1847

A novel one-pot synthesis of isomeric naphtho[1,2-d]isoxazole 2-oxide and naphtho[1,8-de][1,2]oxazine ring systems. A case of simultaneous o- and peri-cyclisation in naphthalene

Author keywords

Hydroxylation; Lead and compounds; N oxides; Naphthalenes; Oxidation; Oximes

Indexed keywords

ISOXAZOLE DERIVATIVE; LEAD; NAPHTHALENE DERIVATIVE; NAPHTHOL DERIVATIVE; OXAZINE DERIVATIVE;

EID: 0034635811     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00029-0     Document Type: Article
Times cited : (20)

References (20)
  • 10
    • 0343823283 scopus 로고    scopus 로고
    • Experimental procedures: (a) A stirred solution of 2-hydroxy-1-naphthaldehyde oxime 1 (5 g, 26.7 mmol) in tetrahydrofuran (60 mL) under argon was cooled to -5°C. LTA (23.7 g, 53.4 mmol) was added slowly over a period of 45 min. The mixture was allowed to reach room temperature and then filtered. The solid was washed with tetrahydrofuran and the filtrate was evaporated in vacuo. The residue was purified by flash chromatography (25%, 50% dichloromethane/hexane, 30% ethyl acetate/hexane) to give 2 (1.7 g, 35%) and 3 (2.1 g, 42%).
    • (a) A stirred solution of 2-hydroxy-1-naphthaldehyde oxime 1 (5 g, 26.7 mmol) in tetrahydrofuran (60 mL) under argon was cooled to -5°C. LTA (23.7 g, 53.4 mmol) was added slowly over a period of 45 min. The mixture was allowed to reach room temperature and then filtered. The solid was washed with tetrahydrofuran and the filtrate was evaporated in vacuo. The residue was purified by flash chromatography (25%, 50% dichloromethane/hexane, 30% ethyl acetate/hexane) to give 2 (1.7 g, 35%) and 3 (2.1 g, 42%).
  • 11
    • 0342518032 scopus 로고    scopus 로고
    • 4) and the solvent was removed in vacuo. The residue was purified by flash chromatography (50%, ethyl acetate/hexane) to give 4 (0.15 g, 70%).
    • 4) and the solvent was removed in vacuo. The residue was purified by flash chromatography (50%, ethyl acetate/hexane) to give 4 (0.15 g, 70%).
  • 13
    • 0343823281 scopus 로고    scopus 로고
    • Note
    • 2 requires: 185.0477.
  • 14
    • 0000652398 scopus 로고
    • and references cited therein.
    • Criegee, R. Angew. Chem. 1958, 70, 173, and references cited therein.
    • (1958) Angew. Chem. , vol.70 , pp. 173
    • Criegee, R.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.