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Volumn 14, Issue 2, 2008, Pages 621-636

Synthesis of 4-aminotropones from [(sulfinyl or sulfonyl)methyl]- substituted p-quinamines

Author keywords

4 aminotropones; Diels Alder reactions; Quinamine; Quinonimine ketal; Sulfones; Sulfoxides

Indexed keywords

AMINOTROPONES; DIELS-ALDER REACTIONS; KETAL HYDROLYSIS; LITHIUM SULFINYL CARBANION; REGIOCONTROLLED ACCESS;

EID: 38149076357     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200700940     Document Type: Article
Times cited : (13)

References (78)
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    • Compound 26 has a high tendency to decompose to the corresponding naphthoquinone dimethyl monoketal. When such a naphthoquinone monoketal was contaminating naphthoquinoneimine monoketal 26, the reaction with the lithium anion of methyl p-tolylsulfoxide gave mixtures of 26 and the known 4-[(p-tolylsulfinyl)methyl]-4naphthoquinol (mixture of epimers) see: M. C. Carreño. M. Pérez González. K. N. Houk, J. Org. Chem. 1997, 62, 9128-9137.
    • Compound 26 has a high tendency to decompose to the corresponding naphthoquinone dimethyl monoketal. When such a naphthoquinone monoketal was contaminating naphthoquinoneimine monoketal 26, the reaction with the lithium anion of methyl p-tolylsulfoxide gave mixtures of 26 and the known 4-[(p-tolylsulfinyl)methyl]-4naphthoquinol (mixture of epimers) see: M. C. Carreño. M. Pérez González. K. N. Houk, J. Org. Chem. 1997, 62, 9128-9137.
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    • Tropone 10 was isolated as a pale-yellow solid, and its structure was confirmed by X-ray crystallographic analysis.
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    • t = 26.5min: This required the synthesis of the racemic 68.
    • t = 26.5min: This required the synthesis of the racemic 68.
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    • The structure of 69a was determined by X-ray crystallographic analysis.
    • The structure of 69a was determined by X-ray crystallographic analysis.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.