Literature DB >> 27976760

Benzimidazopurine nucleosides from N6-aryl adenosine derivatives by PhI(OAc)2-mediated C-N bond formation, no metal needed.

Sakilam Satishkumar1, Mahesh K Lakshman2.   

Abstract

The reaction of a variety of N6-aryl 2'-deoxyadenosine and adenosine derivatives with PhI(OAc)2 in 1,1,1,3,3,3-hexafluoro-2-propanol provides a facile access to benzimidazopurine nucleoside analogues by metal-free C-N bond formation with a purinyl nitrogen atom. These reactions likely proceed via radical-cation/radical processes as indicated by radical inhibition experiments.

Entities:  

Mesh：

Substances：

Year:  2017        PMID： 27976760      PMCID： PMC5309161          DOI： 10.1039/c6cc07722f

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  29 in total

1.  Substituent electronic effects govern direct intramolecular C-N cyclization of N-(Biphenyl)pyridin-2-amines induced by hypervalent iodine(III) reagents.

Authors:  Jean-Ho Chu; Wen-Ting Hsu; Yi-Hua Wu; Meng-Fan Chiang; Nan-Hai Hsu; Hao-Ping Huang; Ming-Jung Wu
Journal:  J Org Chem       Date:  2014-11-18       Impact factor: 4.354

2.  Organocatalytic, oxidative, intramolecular C-H bond amination and metal-free cross-amination of unactivated arenes at ambient temperature.

Authors:  Andrey P Antonchick; Rajarshi Samanta; Katharina Kulikov; Jonas Lategahn
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-26       Impact factor: 15.336

3.  A metal-free tandem demethylenation/C(sp2)-H cycloamination process of N-benzyl-2-aminopyridines via C-C and C-N bond cleavage.

Authors:  Dongdong Liang; Yimiao He; Lanying Liu; Qiang Zhu
Journal:  Org Lett       Date:  2013-06-26       Impact factor: 6.005

4.  Advances in Synthetic Applications of Hypervalent Iodine Compounds.

Authors:  Akira Yoshimura; Viktor V Zhdankin
Journal:  Chem Rev       Date:  2016-02-10       Impact factor: 60.622

5.  Introduction of a hydroxy group at the para position and N-iodophenylation of N-arylamides using phenyliodine(III) bis(trifluoroacetate).

Authors:  Naoki Itoh; Takeshi Sakamoto; Etsuko Miyazawa; Yasuo Kikugawa
Journal:  J Org Chem       Date:  2002-10-18       Impact factor: 4.354

6.  Oxidative Heterocycle Formation Using Hypervalent Iodine(III) Reagents.

Authors:  Sandip Murarka; Andrey P Antonchick
Journal:  Top Curr Chem       Date:  2016

7.  Direct acetoxylation and etherification of anilides using phenyliodine bis(trifluoroacetate).

Authors:  Huan Liu; Xuemin Wang; Yonghong Gu
Journal:  Org Biomol Chem       Date:  2011-01-18       Impact factor: 3.876

8.  Intramolecular cyclization with nitrenium ions generated by treatment of N-acylaminophthalimides with hypervalent iodine compounds: formation of lactams and spiro-fused lactams.

Authors:  Yasuo Kikugawa; Akira Nagashima; Takeshi Sakamoto; Etsuko Miyazawa; Megumi Shiiya
Journal:  J Org Chem       Date:  2003-08-22       Impact factor: 4.354

Review 9.  Advances in the development of nucleoside and nucleotide analogues for cancer and viral diseases.

Authors:  Lars Petter Jordheim; David Durantel; Fabien Zoulim; Charles Dumontet
Journal:  Nat Rev Drug Discov       Date:  2013-06       Impact factor: 84.694

10.  Purinyl N1-directed aromatic C-H oxidation in 6-arylpurines and 6-arylpurine nucleosides.

Authors:  Raghu Ram Chamala; Damon Parrish; Padmanava Pradhan; Mahesh K Lakshman
Journal:  J Org Chem       Date:  2013-07-11       Impact factor: 4.354
View more
  2 in total

1.  Pd-catalyzed versus uncatalyzed, PhI(OAc)2-mediated cyclization reactions of N6-([1,1'-biaryl]-2-yl)adenine nucleosides.

Authors:  Sakilam Satishkumar; Suresh Poudapally; Prasanna K Vuram; Venkateshwarlu Gurram; Narender Pottabathini; Dellamol Sebastian; Lijia Yang; Padmanava Pradhan; Mahesh K Lakshman
Journal:  ChemCatChem       Date:  2017-10-24       Impact factor: 5.686

2.  When nucleoside chemistry met hypervalent iodine reagents.

Authors:  Mahesh K Lakshman; Barbara Zajc
Journal:  ARKIVOC       Date:  2017-12-21       Impact factor: 1.140
  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.