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Volumn , Issue 21, 2004, Pages 4397-4404

Synthesis and rearrangement of N-organyloxy β-lactams derived from a (4+2)/(3+2) sequential cycloaddition reaction involving enol ethers and nitro alkenes

Author keywords

Lactams; Cycloaddition; High pressure chemistry; Multicomponent reactions; Rearrangement

Indexed keywords

1,8 DIPHENYLPERHYDROAZETOL[1,2 B]CYCLOPENTA[E][1,2]OXAZIN 2 ONE; 2 (4 METHOXYBENZYLOXY) 4,5 DIPHENYLPERHYDROAZETO[1,2 B][1,2]OXAZIN 6 ONE; 2 (4 METHOXYBENZYLOXYPERHYDROAZETO[1,2 B][1,2]OXAZIN 6 ONE; 2A,7 DIPHENYLPERHYDROFURO[3',2':5,6] PYRANO[3,2 B]AZET 2 ONE; 3A METHOXY 2A,7 DIPHENYLPERHYDROCYCLOPENTA[5,6]PYRANO[3,2 B]AZET 2 ONE; 4 (4 METHOXYBENZYLOXYL) 2A,6 DIPHENYLPERHYDROPYRANO[3,2 B]AZET 2 ONE; 4A METHOXY 1,8 DIPHENYLPERHYDROAZETO[1,2 B]CYCLOPENTA[E][1,2]OXAZIN 2 ONE; BETA LACTAM; UNCLASSIFIED DRUG;

EID: 8144230739     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400371     Document Type: Article
Times cited : (18)

References (32)
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    • Crystallographic data for the structures 3, 11, and 14 have been deposited with the Cambridge Crystallography Data Centre as supplementary publication numbers CCDC-239386, CCDC-239387, and CCDC-239388 respectively. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: (internat.) +44(0)-1223-336033 or E-mail: deposit@ccdc.cam.ac.uk).
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    • note
    • Using a catalytic amount of base the reaction did not go to completion.
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    • note
    • In the presence of the weak base triethylamine the formation of 8 may also go in a more concerted fashion.
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    • note
    • Treatment of the lactam 6 with dimethylamine for 2 h gave 56% conversion into the lactam 10 (Scheme 5).
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    • note
    • Unfortunately all attempts to isolate the intermediate nitroso acetals failed, because evaporation of solvent in vacuo caused decomposition.
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    • A similar intermolecular reaction was observed upon treatment of N-tosyl-β-lactams with triethylamine in the presence of a nucleophile to give 3-substituted lactams in moderate yield. [16a] C. M. Garparski, M. Teng, M. J. Miller, J. Am. Chem. Soc. 1992, 114, 2741-2743. [16b] M. Teng, M. J. Miller, J. Am. Chem. Soc. 1993, 115, 548-554. [16c] J. R. Bellettini, M. J. Miller, J. Org. Chem. 1996, 61, 7959-7962.
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    • A similar intermolecular reaction was observed upon treatment of N-tosyl-β-lactams with triethylamine in the presence of a nucleophile to give 3-substituted lactams in moderate yield. [16a] C. M. Garparski, M. Teng, M. J. Miller, J. Am. Chem. Soc. 1992, 114, 2741-2743. [16b] M. Teng, M. J. Miller, J. Am. Chem. Soc. 1993, 115, 548-554. [16c] J. R. Bellettini, M. J. Miller, J. Org. Chem. 1996, 61, 7959-7962.
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    • A similar intermolecular reaction was observed upon treatment of N-tosyl-β-lactams with triethylamine in the presence of a nucleophile to give 3-substituted lactams in moderate yield. [16a] C. M. Garparski, M. Teng, M. J. Miller, J. Am. Chem. Soc. 1992, 114, 2741-2743. [16b] M. Teng, M. J. Miller, J. Am. Chem. Soc. 1993, 115, 548-554. [16c] J. R. Bellettini, M. J. Miller, J. Org. Chem. 1996, 61, 7959-7962.
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    • note
    • Under the basic reaction conditions the aldehyde probably reacts further.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.