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Volumn , Issue 13, 2005, Pages 2715-2733

The dipolar route to azepin-3-one derivatives by heterocyclization of linear and monocyclic enallenyl nitrones as the key step

Author keywords

Allenes; Azepinones; Electrocyclization; Nitrones; Photochemistry

Indexed keywords


EID: 22144471909     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400922     Document Type: Article
Times cited : (21)

References (73)
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    • note
    • The bromo formylation procedure gave an approximately 10:1 (E)/(Z) mixture of 12, which could not be separated by chromatography. However, subsequent reaction of this mixture afforded the nitrone 16 with no detectable amounts of the corresponding (E) isomer.
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    • Access by photochemical transformation of an oxaziridine precursor to a derivative of a benzo-annulated pyrrolidinoazepin-3-one with a saturated C-6-C-7 bond and a methyl group at the C-11b position has been described: G. P. Johnson, B. A. Marples, Tetrahedron Lett. 1985, 26, 4115-4118.
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    • CCDC-262102 (for 37), CCDC-262103 (for 43), and CCDC-262104 (for 47) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
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    • note
    • The relatively low yield of 49 (37%) is partly due to the formation of two side-products, namely the primary alcohol of 28 (ca. 20%, isolated as a mixture with 49), obtained by a Grignard reduction process, and a higher molecular compound (ca. 15%, not isolated), which probably comes from the reaction of 28 with the 1,4-bis-Grignard reagent of butane.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.