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Volumn 59, Issue 36, 2003, Pages 7103-7110

An alternative approach towards novel heterocycle-fused 1, 4-diazepin-2-ones by an aromatic amidation protocol

Author keywords

Cyclizations; Diazepin 2 ones; Heterocycles; Hypervalent iodine; N acylnitrenium

Indexed keywords

3 (4 ETHOXYCARBONYL) 1 METHOXY 3 METHYL 1,3,4,5 TETRAHYDRO 2H 1,4 THIENO[3,2 F]DIAZEPIN 2 ONE; 4 ETHOXYCARBONYL 1 METHOXY 1,3,4,5 TETRAHYDRO 2H 1,4 THIENO[3,2 F]DIAZEPIN 2 ONE; 4 ETHOXYCARBONYL 1 METHOXY 1,3,4,5 TETRAHYDRO 2H [1,4]BENZODIAZEPIN 2 ONE; 4 ETHOXYCARBONYL 1 METHOXY 3 METHYL 1,3,4,5 TETRAHYDRO 2H [1,4]BENZODIAZEPIN 2 ONE; 4 ETHOXYCARBONYL 1 METHOXY N' METHYL 1,3,4,5 TETRAHYDRO 2H 1,4 PYRROLO[2,3 F]DIAZEPIN 2 ONE; ACETIC ACID DERIVATIVE; ALANINE; AMIDE; AMINO ACID; DIAZEPINE DERIVATIVE; GLYCINE; ION; METHOXYAMIDE; N ACYLNITRENIUM ION; PHENYLIODINE BIS(TRIFLUOROACETATE); UNCLASSIFIED DRUG;

EID: 0042020360     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)01123-2     Document Type: Article
Times cited : (34)

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    • This substrate was prepared following standard procedures by reductive amination of benzaldehyde with alanine methyl ester. Spectroscopic data of compound
    • This substrate was prepared following standard procedures by reductive amination of benzaldehyde with alanine methyl ester. Spectroscopic data of compound 3b can be found in: Szilágyi L., Györgydeák Z. J. Am. Chem. Soc. 101:1979;427-432.
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    • 2O was employed for the hydrolysis of ester (S)-7b to avoid, as detected under other conditions, racemization at this stage.
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    • These antitumoral antiobiotics have been isolated from Streptomyces species. Their therapeutic activity is due to their ability to combine with specific sequences of DNA. See for example:
    • These antitumoral antiobiotics have been isolated from Streptomyces species. Their therapeutic activity is due to their ability to combine with specific sequences of DNA. See for example: Mountzouris J.A., Wang J.J., Thurston D.E., Hurley L.H. J. Med. Chem. 37:1994;3132-3140.
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    • 2 complete degradation of the starting material was observed. Since, in this case, the use of trifluoroethanol made a significant improvement, the transformation of amide 5c into diazepine 6c was also attempted but with no success.


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