Intramolecular Azide to Alkene Cycloadditions for the Construction of Pyrrolobenzodiazepinesand Azetidino-Benzodiazepines

Molecules

Christopher S. Chambers¹  Karl Hemming¹  Faisal Jamshaid¹  Paul A. O'Gorman¹ 

[1] Department of Chemical Sciences, University of Huddersfield, Queensgate, Huddersfield,West Yorkshire HD1 3DH, UK;

关键词: cycloaddition;    1,3-dipole;    azide;    pyrrolobenzodiazepine;    azetidinone;    antitumour;    antibiotic;    β-lactam;   

DOI  :  10.3390/molecules191016737

来源: DOAJ

【 摘 要 】

The coupling of proline- and azetidinone-substituted alkenes to 2-azidobenzoic and 2-azidobenzenesulfonic acid gives precursors that undergo intramolecular azide to alkene 1,3-dipolar cycloadditions to give imine-, triazoline- or aziridine-containing pyrrolo[1,4]benzodiazepines (PBDs), pyrrolo[1,2,5]benzothiadiazepines (PBTDs), and azetidino[1,4]benzodiazepines. The imines and aziridines are formed after loss of nitrogen from a triazoline cycloadduct. The PBDs are a potent class of antitumour antibiotics.

【 授权许可】

Unknown