Journal ArticleDOI
An Efficient Synthesis of Highly Functionalised 4‐Substituted 2‐Azetidinones by a Stereoselective Intermolecular Diels−Alder Reaction of Different Types of 2‐Azetidinone‐Tethered Dienes
Benito Alcaide,Pedro Almendros,Nati R. Salgado,Mari Paz Martinez-Alcazar,Félix Hernández-Cano +4 more
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TLDR
Intermolecular Diels−Alder reaction of 2-azetidinone-tethered dienes with cyclic dienophiles such as N-methyl and N-phenylmaleimide proceeded with modest endo/exo diastereoselectivity.About:
This article is published in European Journal of Organic Chemistry.The article was published on 2001-05-01. It has received 14 citations till now. The article focuses on the topics: Diels–Alder reaction & Dimethyl acetylenedicarboxylate.read more
Citations
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Journal ArticleDOI
Additions of Allenyl/Propargyl Organometallic Reagents to 4-Oxoazetidine-2-carbaldehydes: Novel Palladium-Catalyzed Domino Reactions in Allenynes
TL;DR: An unprecedented one-pot stereoselective synthesis of beta-chlorinated allylic alcohols, which can be considered as functionalized allylsilanes, has been developed, which involves tin(IV) chloride-mediated reaction of propargyltrimethylsilane and 4-oxoazetidine-2-carbaldehydes.
Journal ArticleDOI
Exploring the Solid-Phase Synthesis of 3,4-Disubstituted β-Lactams: Scope and Limitations
TL;DR: This work describes a comprehensive study on the solid-phase synthesis of 3,4-disubstituted beta-lactams, with the cost-effective Wang resin proving to be the most effective and the utility of the protocol demonstrated by the highly efficient asymmetric versions when homochiral ketenes or Homochiral aldimines were used.
Book ChapterDOI
Novel and Recent Synthesis and Applications of β-Lactams
TL;DR: In this chapter, a comprehensive overview of the most significant and interesting contributions published from 2000 until now, concerning the preparation of novel β-lactam structures is presented and among the different synthetic strategies available, either novel or already known but efficient and versatile methodologies are covered.
Journal ArticleDOI
Stereoselective synthesis of trans- and cis-2-aryl-3-(hydroxymethyl)aziridines through transformation of 4-aryl-3-chloro-β-lactams and study of their ring opening
TL;DR: Trans- and cis-1-Alkyl-4-aryl-3-chloroazetidin-2-ones, prepared through cyclocondensation of chloroketene and the appropriate imines in a diastereoselective way, were transformed into the corresponding non-activated trans- and bis(hydroxymethyl)aziridines via reductive ring contraction using LiAlH(4) in Et(2)O.
References
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BookDOI
The Chemistry of β-lactams
TL;DR: The biosynthesis of beta-lactams, J.E. Baldwin and C.C. Schofield structure-activity relationships - chemical, M.I. Page mode of action - interaction with the penicillin binding proteins, S.G. Waley beta- lactamase - inhibition, R.D. Page - biological.
Journal ArticleDOI
Synthetic Inhibitors of Elastase
TL;DR: The peptidyl TFMK ICI 200,880 has many of the desired characteristics of a drug to treat the diseases associated with HNE: chemical stability, in vitro and in vivo activity, a long duration of action, and adequate metabolic stability.
Journal ArticleDOI
Azetidin-2-one derivatives as inhibitors of thrombin.
Han William T,Ashok K. Trehan,J. J. Kim Wright,Marianne E. Federici,Steven M. Seiler,Nicholas A. Meanwell +5 more
TL;DR: Activity in this assay did not correlate well with inhibition of thrombin-induced cleavage of a synthetic substrate, presumably a consequence of inherent chemical instability and degradation in plasma.
Journal ArticleDOI
Design and synthesis of monocyclic β-lactams as mechanism-based inhibitors of human cytomegalovirus protease
Alan D. Borthwick,Gordon G. Weingarten,Terry M. Haley,Mirek Tomaszewski,Wei Wang,Zhouhan Hu,Jean Bedard,Haloun Jin,Leonard Yuen,Tarek S. Mansour +9 more
TL;DR: SAR in a series of monocyclic beta-lactam N-ureas, has defined the size and relative stereochemistry of the C-3 substituent producing a low micromolar inhibitor 17b with good aqueous stability and selectivity over the mammalian serine proteases.