Literature DB >> 22572739

Nitrous oxide as a primary product in base-mediated β-elimination reactions of diazeniumdiolated benzylamine derivatives.

Debanjan Biswas1, Zhao Cao, Larry K Keefer, Joseph E Saavedra.   

Abstract

We report an unexpected β-elimination pathway by which diazeniumdiolated benzylamines of structure Bn-N(R)-N(O)=N-OR' undergo base-mediated fragmentation to generate N(2)O as the only gaseous product. The reaction is especially rapid for R = 2-hydroxyethyl, in which the hydroxyl group anchimerically assists benzylic proton removal with concomitant expulsion of PhCH=NR and R'OH.

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Year:  2012        PMID： 22572739      PMCID： PMC6959517          DOI： 10.1039/c2cc32284f

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


  10 in total

Review 1.  Chemistry of the nitric oxide-releasing diazeniumdiolate ("nitrosohydroxylamine") functional group and its oxygen-substituted derivatives.

Authors:  Joseph A Hrabie; Larry K Keefer
Journal:  Chem Rev       Date:  2002-04       Impact factor: 60.622

2.  Variable C2-symmetric analogues of N-hydroxyphthalimide as enantioselective catalysts for aerobic oxidation: kinetic resolution of oxazolidines.

Authors:  Malek Nechab; Dhondi Naveen Kumar; Christian Philouze; Cathy Einhorn; Jacques Einhorn
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

3.  Targeting nitric oxide (NO) delivery in vivo. Design of a liver-selective NO donor prodrug that blocks tumor necrosis factor-alpha-induced apoptosis and toxicity in the liver.

Authors:  J E Saavedra; T R Billiar; D L Williams; Y M Kim; S C Watkins; L K Keefer
Journal:  J Med Chem       Date:  1997-06-20       Impact factor: 7.446

4.  The secondary amine/nitric oxide complex ion R(2)N[N(O)NO](-) as nucleophile and leaving group in S9N)Ar reactions.

Authors:  J E Saavedra; A Srinivasan; C L Bonifant; J Chu; A P Shanklin; J L Flippen-Anderson; W G Rice; J A Turpin; K M Davies; L K Keefer
Journal:  J Org Chem       Date:  2001-05-04       Impact factor: 4.354

5.  Comparison of the NO and HNO donating properties of diazeniumdiolates: primary amine adducts release HNO in Vivo.

Authors:  Katrina M Miranda; Tatsuo Katori; Claudia L Torres de Holding; Lynta Thomas; Lisa A Ridnour; William J McLendon; Stephanie M Cologna; Andrew S Dutton; Hunter C Champion; Daniele Mancardi; Carlo G Tocchetti; Joseph E Saavedra; Larry K Keefer; K N Houk; Jon M Fukuto; David A Kass; Nazareno Paolocci; David A Wink
Journal:  J Med Chem       Date:  2005-12-29       Impact factor: 7.446

6.  Esterase-sensitive nitric oxide donors of the diazeniumdiolate family: in vitro antileukemic activity.

Authors:  J E Saavedra; P J Shami; L Y Wang; K M Davies; M N Booth; M L Citro; L K Keefer
Journal:  J Med Chem       Date:  2000-01-27       Impact factor: 7.446

7.  Chemistry of the diazeniumdiolates. 2. Kinetics and mechanism of dissociation to nitric oxide in aqueous solution.

Authors:  K M Davies; D A Wink; J E Saavedra; L K Keefer
Journal:  J Am Chem Soc       Date:  2001-06-13       Impact factor: 15.419

8.  O2-(N-hydroxy(methoxy)-2-ethanesulfonamido) protected diazen-1-ium-1,2-diolates: nitric oxide release via a base-induced β-elimination cleavage.

Authors:  Zhangjian Huang; Edward E Knaus
Journal:  Org Lett       Date:  2011-02-09       Impact factor: 6.005

9.  Chemistry of the diazeniumdiolates. O- versus N-alkylation of the RNH[N(O)NO](-) ion.

Authors:  Joseph E Saavedra; D Scott Bohle; Kamilah N Smith; Clifford George; Jeffrey R Deschamps; Damon Parrish; Joseph Ivanic; Yan-Ni Wang; Michael L Citro; Larry K Keefer
Journal:  J Am Chem Soc       Date:  2004-10-13       Impact factor: 15.419

Review 10.  Fifty years of diazeniumdiolate research. From laboratory curiosity to broad-spectrum biomedical advances.

Authors:  Larry K Keefer
Journal:  ACS Chem Biol       Date:  2011-09-30       Impact factor: 5.100
  10 in total

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