Literature DB >> 12919049

5-Endo-dig electrophilic cyclization of alpha-alkynyl carbonyl compounds: synthesis of novel bicyclic 5-iodo- and 5-bromofuranopyrimidine nucleosides.

Meneni Srinivasa Rao1, Noor Esho, Craig Sergeant, Roman Dembinski.   

Abstract

5-Endo-dig electrophilic cyclization of 5-alkynyl-2'-deoxyuridines with N-iodosuccinimide or N-bromosuccinimide in acetone at room temperature gives 3-(2'-deoxy-beta-D-ribofuranosyl)-5-halo-2,3-dihydrofuro[2,3-d]pyrimidin-2-ones that usually precipitate from the reaction mixture (86-74%).

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Year:  2003        PMID： 12919049     DOI： 10.1021/jo0345648

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


  8 in total

1.  Synthesis of 3-iodoindoles by the Pd/Cu-catalyzed coupling of N,N-dialkyl-2-iodoanilines and terminal acetylenes, followed by electrophilic cyclization.

Authors:  Dawei Yue; Tuanli Yao; Richard C Larock
Journal:  J Org Chem       Date:  2006-01-06       Impact factor: 4.354

2.  5-Alkynyl-2'-deoxyuridines: chromatography-free synthesis and cytotoxicity evaluation against human breast cancer cells.

Authors:  Srinivasarao Meneni; Ingo Ott; Craig D Sergeant; Adam Sniady; Ronald Gust; Roman Dembinski
Journal:  Bioorg Med Chem       Date:  2007-02-01       Impact factor: 3.641

3.  Synthesis and EPR studies of 2'-deoxyuridines with alkynyl, rodlike linkages.

Authors:  Adam Sniady; Michael D Sevilla; Srinivasarao Meneni; Tadeusz Lis; Slawomir Szafert; Deepthi Khanduri; John M Finke; Roman Dembinski
Journal:  Chemistry       Date:  2009-08-03       Impact factor: 5.236

4.  Metal-catalyzed 1,2-shift of diverse migrating groups in allenyl systems as a new paradigm toward densely functionalized heterocycles.

Authors:  Alexander S Dudnik; Anna W Sromek; Marina Rubina; Joseph T Kim; Alexander V Kel'in; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2008-01-04       Impact factor: 15.419

5.  4-(4-Bromo-phen-yl)-6-(4-chloro-phen-yl)-pyrimidin-2-ylamine.

Authors:  Mujahid Hussain Bukhari; Hamid Latif Siddiqui; Naveed Ahmad; Waseeq Ahmad Siddiqui; Masood Parvez
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-01-28

6.  Organometallic Nucleosides: Synthesis and Biological Evaluation of Substituted Dicobalt Hexacarbonyl 2'-Deoxy-5-oxopropynyluridines.

Authors:  Renata Kaczmarek; Dariusz Korczyński; Karolina Królewska-Golińska; Kraig A Wheeler; Ferman A Chavez; Agnieszka Mikus; Roman Dembinski
Journal:  ChemistryOpen       Date:  2018-01-18       Impact factor: 2.911

7.  Extension of furopyrimidine nucleosides with 5-alkynyl substituent: Synthesis, high fluorescence, and antiviral effect in the absence of free ribose hydroxyl groups.

Authors:  Renata Kaczmarek; Dylan J Twardy; Trevor L Olson; Dariusz Korczyński; Graciela Andrei; Robert Snoeck; Rafał Dolot; Kraig A Wheeler; Roman Dembinski
Journal:  Eur J Med Chem       Date:  2020-09-28       Impact factor: 6.514

8.  Extension of the 5-alkynyluridine side chain via C-C-bond formation in modified organometallic nucleosides using the Nicholas reaction.

Authors:  Renata Kaczmarek; Dariusz Korczyński; James R Green; Roman Dembinski
Journal:  Beilstein J Org Chem       Date:  2020-01-02       Impact factor: 2.883
  8 in total

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