Literature DB >> 21340084

Microwave promoted C6-alkylation of purines through S(N)Ar-based reaction of 6-chloropurines with 3-alkyl-acetylacetone.

Hai-Ming Guo1, Yu Zhang, Hong-Ying Niu, Dong-Chao Wang, Zhi-Liang Chu, Gui-Rong Qu.   

Abstract

C6-Alkylated purine analogues were obtained in good to excellent isolated yields by S(N)Ar reaction of 6-chloropurine derivatives with 3-alkyl-acetylacetone. 3-Alkyl-acetylacetones were employed as alkylating agents and C6-alkylated purines were obtained highly selectively within short reaction time under microwave irradiation conditions. This work is complementary to the classical coupling reactions for the synthesis of C6-alkylated purine analogues.

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Year:  2011        PMID: 21340084     DOI: 10.1039/c0ob01213k

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  3 in total

1.  Metal-free arylation of ethyl acetoacetate with hypervalent diaryliodonium salts: an immediate access to diverse 3-aryl-4(1H)-quinolones.

Authors:  Andrii Monastyrskyi; Niranjan K Namelikonda; Roman Manetsch
Journal:  J Org Chem       Date:  2015-02-24       Impact factor: 4.354

2.  Synthesis of C6-Substituted Purine Nucleoside Analogues via Late-Stage Photoredox/Nickel Dual Catalytic Cross-Coupling.

Authors:  James J Perkins; Valerie W Shurtleff; Alayna M Johnson; Abdellatif El Marrouni
Journal:  ACS Med Chem Lett       Date:  2021-03-08       Impact factor: 4.345

3.  1,2,3-Triazoles as leaving groups: SNAr reactions of 2,6-bistriazolylpurines with O- and C-nucleophiles.

Authors:  Dace Cīrule; Irina Novosjolova; Ērika Bizdēna; Māris Turks
Journal:  Beilstein J Org Chem       Date:  2021-02-11       Impact factor: 2.883

  3 in total

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