Integrated Ugi-based assembly of functionally, skeletally, and stereochemically diverse 1,4-benzodiazepin-2-ones.
نویسندگان
چکیده
A practical, integrated and versatile U-4CR-based assembly of 1,4-benzodiazepin-2-ones exhibiting functionally, skeletally, and stereochemically diverse substitution patterns is described. By virtue of its convergence, atom economy, and bond-forming efficiency, the methodology documented herein exemplifies the reconciliation of structural complexity and experimental simplicity in the context of medicinal chemistry projects.
منابع مشابه
An expedient and facile route for the general synthesis of 3-aryl substituted 1,2,3-triazolo[1,5-a][1,4]benzodiazepin-6-ones and 1,2,3-triazolo[1,5-a][1,5]benzodiazocin-7-ones.
We describe herein a convenient approach for the general synthesis of novel tricyclic scaffolds incorporating a fusion of the 1,2,3-triazole ring with difficultly obtainable medium sized rings such as [1,4]benzodiazepin-5-ones and [1,5]benzodiazocin-6-ones through Sonogashira coupling of an aryl iodide with 2-amino-N-methyl-N-(prop-2-ynyl)benzamide or homologue followed by in situ diazotisation...
متن کاملLate stage C H activation of a privileged scaffold; synthesis ― of a library of benzodiazepines
A library of over twenty 5-(2-arylphenyl)1,3-dihydro-2H-1,4-benzodiazepin-2-ones has been formed by a microwave-mediated late-stage palladium-catalysed arylation of 1,4-benzodiazepines using diaryliodonium salts. This can also be applied to nordazepam (7-chloro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one), the active metabolite of diazepam, and subsequent N-alkylation and/or H/D exchange al...
متن کاملEffect of 3-substituted 1,4-benzodiazepin-2-ones on bradykinin-induced smooth muscle contraction.
Biochemical properties of 3-substituted 1,4-benzodiazepine determined by the characteristics of their chemical structure. Influence of 3-substituted 1,4-benzodiazepin-2-ones on maximal normalized rate and amplitudes of isometric smooth muscle contraction in rats was investigated. Compounds MX-1775 and MX-1828 demonstrated the similar inhibition effect on bradykinin-induced contraction of smooth...
متن کاملMethane negative chemical ionization analysis of 1,3-dihydro-5-phenyl-1,4-benzodiazepin-2-ones.
The methane negative chemical ionization (NCI) mass spectra of the medically important 1,3-dihydro-5-phenyl-1,4-benzodiazepin-2-ones generally consisted solely of M- and (M-H)- ions. Attempts to find the location of the H lost in the generation of the (M-H)- ion were unsuccessful, although many possibilities were eliminated. A Hammett correlation analysis of the relative sensitivities of a seri...
متن کاملSolubility of selected derivatives of 1,4-benzodiazepine-2-one in the presence of PVP.
Pharmaceutical availability of diazepam, oxazepam and nitrazepam from solid dispersions of PVP have been studied in comparison to those of the corresponding physical mixtures and pure benzodiazepines. The derivatives of 1,4-benzodiazepin-2-one are poorly water soluble drugs. The properties of diazepam-, oxazepam- and nitrazepam-PVP solid dispersions have been determined by the methods of differ...
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ورودعنوان ژورنال:
- The Journal of organic chemistry
دوره 80 3 شماره
صفحات -
تاریخ انتشار 2015