Literature DB >> 30547589

Access to 2,3-Fused Pyrroles via Visible Light Driven Coupling of α-Azidochalcones with 1/2-Naphthols, or 2-Hydroxy-1,4-Naphthoquinone.

Satheesh Borra1,2, D Chandrasekhar1,2, Uma Devi Newar1, Ram Awatar Maurya1,2.   

Abstract

α-Azidochalcones were coupled with 1/2-naphthols or 2-hydroxy-1,4-naphthoquinone using Ru(bpy)3(PF6)2 as a photocatalyst under blue LED light irradiation to yield 2,3-fused pyrroles in high yields (68-84%). The overall transformation involves photosensitized decomposition of α-azidochalcones into highly reactive 2 H-azirines which are trapped by 1/2-naphthols or 2-hydroxy-1,4-naphthoquinone, leading to the construction of two new C-N and one new C-C bonds.

Entities:  

Year:  2018        PMID： 30547589     DOI： 10.1021/acs.joc.8b02459

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


  4 in total

Review 1.  Vinylazides: versatile synthons and magical precursors for the construction of N-heterocycles.

Authors:  Zahra Tashrifi; Mohammad Mohammadi-Khanaposhtani; Bagher Larijani; Halleh Hamedifar; Samira Ansari; Mohammad Mahdavi
Journal:  Mol Divers       Date:  2020-05-30       Impact factor: 2.943

2.  An efficient and targeted synthetic approach towards new highly substituted 6-amino-pyrazolo[1,5-a]pyrimidines with α-glucosidase inhibitory activity.

Authors:  Fariba Peytam; Mehdi Adib; Reihaneh Shourgeshty; Loghman Firoozpour; Mahmoud Rahmanian-Jazi; Mehdi Jahani; Setareh Moghimi; Kouros Divsalar; Mohammad Ali Faramarzi; Somayeh Mojtabavi; Fatemeh Safari; Mohammad Mahdavi; Alireza Foroumadi
Journal:  Sci Rep       Date:  2020-02-13       Impact factor: 4.379

3.  Copper(II)-Catalyzed (3+2) Cycloaddition of 2H-Azirines to Six-Membered Cyclic Enols as a Route to Pyrrolo[3,2-c]quinolone, Chromeno[3,4-b]pyrrole, and Naphtho[1,8-ef]indole Scaffolds.

Authors:  Pavel A Sakharov; Nikolai V Rostovskii; Alexander F Khlebnikov; Mikhail S Novikov
Journal:  Molecules       Date:  2022-09-02       Impact factor: 4.927

4.  Design, synthesis, molecular docking, and in vitro α-glucosidase inhibitory activities of novel 3-amino-2,4-diarylbenzo[4,5]imidazo[1,2-a]pyrimidines against yeast and rat α-glucosidase.

Authors:  Fariba Peytam; Ghazaleh Takalloobanafshi; Toktam Saadattalab; Maryam Norouzbahari; Zahra Emamgholipour; Setareh Moghimi; Loghman Firoozpour; Hamid Reza Bijanzadeh; Mohammad Ali Faramarzi; Somayeh Mojtabavi; Parviz Rashidi-Ranjbar; Saeed Karima; Roya Pakraad; Alireza Foroumadi
Journal:  Sci Rep       Date:  2021-06-07       Impact factor: 4.379
  4 in total

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