Literature DB >> 29528633

[2+2]-Photocycloaddition of N-Benzylmaleimide to Alkenes As an Approach to Functional 3-Azabicyclo[3.2.0]heptanes.

Yevhen A Skalenko1,2, Tetiana V Druzhenko1,2, Aleksandr V Denisenko1,3, Maryna V Samoilenko1, Oleksandr P Dacenko1, Serhii A Trofymchuk1, Oleksandr O Grygorenko1,3, Andrey A Tolmachev1,3, Pavel K Mykhailiuk1,3.   

Abstract

A one-step synthesis of functionalized 3-azabicyclo[3.2.0]heptanes by [2+2]-photochemical intermolecular cycloaddition of N-benzylmaleimide to alkenes was elaborated. The obtained compounds were easily transformed into the bi- and tricyclic analogues of piperidine, morpholine, piperazine, and GABA, which are advanced building blocks for drug discovery.

Entities:  

Year:  2018        PMID: 29528633     DOI: 10.1021/acs.joc.8b00077

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  2 in total

1.  Escaping from Flatland: [2 + 2] Photocycloaddition; Conformationally Constrained sp3-rich Scaffolds for Lead Generation.

Authors:  Brian Cox; Kevin I Booker-Milburn; Luke D Elliott; Michael Robertson-Ralph; Victor Zdorichenko
Journal:  ACS Med Chem Lett       Date:  2019-10-22       Impact factor: 4.345

2.  Intramolecular thiomaleimide [2 + 2] photocycloadditions: stereoselective control for disulfide stapling and observation of excited state intermediates by transient absorption spectroscopy.

Authors:  Roshni Malde; Michael A Parkes; Michael Staniforth; Jack M Woolley; Vasilios G Stavros; Vijay Chudasama; Helen H Fielding; James R Baker
Journal:  Chem Sci       Date:  2022-01-28       Impact factor: 9.825

  2 in total

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