Literature DB >> 16524274

Regioselective synthesis of N-beta-hydroxyethylaziridines by the ring-opening reaction of epoxides with aziridine generated in situ.

Ha Young Kim1, Arindam Talukdar, Mark Cushman.   

Abstract

[reaction: see text] Biologically important N-beta-hydroxyethylaziridine intermediates were conveniently prepared by regioselective ring-opening reactions of diversely substituted epoxides. Ethyleneimine generated in situ under basic conditions from beta-chloroethylamine was used as a nucleophile to open the epoxides in an aqueous environment.

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Year:  2006        PMID： 16524274      PMCID： PMC2597441          DOI： 10.1021/ol0529703

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  8 in total

1.  Synthesis of a chiral aziridine derivative as a versatile intermediate for HIV protease inhibitors.

Authors:  B M Kim; S J Bae; S M So; H T Yoo; S K Chang; J H Lee; J Kang
Journal:  Org Lett       Date:  2001-07-26       Impact factor: 6.005

2.  Enantioselective catalytic aziridinations and asymmetric nitrene insertions into CH bonds.

Authors:  Paul Müller; Corinne Fruit
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

3.  "On water": unique reactivity of organic compounds in aqueous suspension.

Authors:  Sridhar Narayan; John Muldoon; M G Finn; Valery V Fokin; Hartmuth C Kolb; K Barry Sharpless
Journal:  Angew Chem Int Ed Engl       Date:  2005-05-20       Impact factor: 15.336

Review 4.  Atenolol: a review of its pharmacological properties and therapeutic efficacy in angina pectoris and hypertension.

Authors:  R C Heel; R N Brogden; T M Speight; G S Avery
Journal:  Drugs       Date:  1979-06       Impact factor: 9.546

5.  Epoxides and aziridines from diazoacetates via ylide intermediates.

Authors:  M P Doyle; W Hu; D J Timmons
Journal:  Org Lett       Date:  2001-03-22       Impact factor: 6.005

6.  Synthesis of chiral amino epoxyaziridines: useful intermediates for the preparation of chiral trisubstituted piperidines.

Authors:  José M Concellón; Estela Riego; Ignacio A Rivero; Adrián Ochoa
Journal:  J Org Chem       Date:  2004-09-17       Impact factor: 4.354

7.  Guanidines as a nitrogen source for direct conversion of epoxides to aziridines.

Authors:  Yukiko Tsuchiya; Takuya Kumamoto; Tsutomu Ishikawa
Journal:  J Org Chem       Date:  2004-11-26       Impact factor: 4.354

8.  Synthesis and evaluation of novel electrophilic nitrofuran carboxamides and carboxylates as radiosensitizers and bioreductively activated cytotoxins.

Authors:  M A Naylor; M A Stephens; S Cole; M D Threadgill; I J Stratford; P O'Neill; E M Fielden; G E Adams
Journal:  J Med Chem       Date:  1990-09       Impact factor: 7.446
  8 in total
  1 in total

Review 1.  Facile and Green Synthesis of Saturated Cyclic Amines.

Authors:  Arruje Hameed; Sadia Javed; Razia Noreen; Tayyaba Huma; Sarosh Iqbal; Huma Umbreen; Tahsin Gulzar; Tahir Farooq
Journal:  Molecules       Date:  2017-10-12       Impact factor: 4.411
  1 in total

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