Synthesis of Heterocycles from Oximes

Abstract

Introduction Synthesis of Heterocyclic Compounds from Oximes Conclusions

Gold(I)-Catalyzed Enantioselective Annulations between Allenes and Alkene-Tethered Oxime Ethers: A Straight Entry to Highly Substituted Piperidines and aza-Bridged Medium-Sized Carbocycles

“…Moreover, both cis and trans oxime isomers are configurationally stable and potentially accessible . No less important, the N–O bond that is present in the products should provide for further elaboration into a variety of piperidine derivatives …”

Oximes of Seven-Membered Heterocyclic Compounds Containing One Heteroatom

“…The recent advances in the synthesis of heterocyclic systems have been described in the reviews [58,59]. In this chapter, specific reactions involving cyclization of oximes of seven-membered heterocyclic compounds containing one heteroatom will be set out in details.…”

“…Thus, interaction of azepine oxime ether 58 with a mixture of formic and phosphoric acids at 60 о С affords 5,7-dihydro-6Н- [1]benzofuro [3,2-d] [1]benzazepin-6-one (59) in the yields up to 74% [44]. The treatment of 3,4-dihydro-4-hydroxymethylen- [1]benzothiepin-5(2Н)-one (60) with hydroxylamine hydrochloride in acetic acid leads to formation of a mixture of isoxazolines 61 and 62.…”

Facile Synthesis of Oxime Amino Ethers via Lewis Acid Catalyzed SN2-Type Ring Opening of Activated Aziridines with Aryl Aldehyde Oximes

“…12 The available reports for the synthesis of oxime ethers mainly involve etherification of oximes 13 -another valuable functional group in organic synthesis. 14 Dehydrogenative cross-coupling reaction between allylic sp 3 C-H bonds with oximes 15 have also been performed to access oxime ethers. In this context, we realized that regio-and stereospecific synthetic routes to functionalized and structurally diverse oxime amino ethers are scarce in the literature which could nonetheless emerge as potential synthons for valuable biologically active compounds.…”