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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 24
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Original Articles

One-Pot Synthesis of N-Alkyl Sulfonyl Hydrazones by Dialkyl Acetylenedicarboxylate-Mediated Reaction of Trialkylphosphites with Sulfonyl Hydrazones

Pages 3352-3356 | Received 14 Sep 2012, Published online: 05 Sep 2013

REFERENCES

  • Sakya , S. M. ; Hou , X. J. ; Minich , M. L. ; Rast , B. ; Shavnya , A. ; DeMello , K. M. L. ; Cheng , H. ; Li , J. ; Jaynes , B. H. ; Mann , D. W. ; Petras , C. F. ; Seibel , S. B. ; Haven , M. L. 5-Heteroatom-substituted pyrazoles as canine COX-2 inhibitors, part 3: Molecular modeling studies on binding contribution of 1-(5-methylsulfonyl)pyrid-2-yl and 4-nitrile . Bioorg. Med. Chem. Lett. 2007 , 17 , 1067 – 1072 .
  • Sasikumar , T. K. ; Qiang , L. ; Burnett , D. A. ; Cole , D. ; Xu , R. ; Li , H. M. ; Greenlee , W. J. ; Clader , J. ; Zhang , L. ; Hyde , L. Tricyclic sulfones as orally active v-secretase inhibitors: Synthesis and structure–activity relationship studies . Bioorg. Med. Chem. Lett. 2010 , 20 , 3632 – 3635 .
  • Di Santo , R. ; Costi , R. ; Artico , N. ; Rango , R. ; Lavecchia , A. ; Novellino , E. ; Gavuzzo , E. ; La Torre , F. ; Cirilli , R. ; Cancio , R. ; Maga , G. Design synthesis, biological evaluation, and molecular modeling studies of TIBO-like cyclic sulfones as non-nucleoside HIV-1 reverse transcriptase inhibitors . Chem. Med. Chem. 2006 , 16 , 82 – 95 .
  • Cheung , W. H. ; Zheng , S. L. ; Yu , W. Y. ; Zhou , G. C. ; Che , C. M. Ruthenium porphyrin–catalyzed intramolecular carbenoid C-H insertion: Stereoselective synthesis of cis-disubstituted oxygen and nitrogen heterocycles . Org. Lett. 2003 , 5 , 2535 – 2538 .
  • Fulton , J. R. ; Aggarwal , V. K. ; de Vicente , J. The use of tosylhydrazone salts as a safe alternation for handling diazo compounds and their applications in organic synthsis . Eur. J. Org. Chem. 2005 , 1479 – 1492 .
  • Aggarwal , V. K. ; de Vicente , J. ; Bonnert , R. V. Catalytic cyclopropanation of alkenes using diazo compounds generated in situ: A novel to 2-arylcyclopropylamines . Org. Lett. 2001 , 3 , 2785 – 2788 .
  • Aggarwal , V. K. ; Bae , I. ; Lee , H. Y. ; Richardson , J. ; Williams , D. T. Sulfur-ylide-mediated synthesis of functionalized and trisubstituted epoxides with high enantioselectivy: Application to the synthesis of CDP-840 . Angew. Chem. Int. Ed. 2003 , 42 , 3274 – 3278 .
  • Movassaghi , M. ; Ahmed , K. O. A stereospecific palladium-catalyzed route to monoalkyl diazenes for mild allylic reduction. Angew. Chem. Int. Ed. 2008, 47, 8909–8912.
  • Schant , G. J. ; Hebeisen , P. ; Karpellus , P. N-Arensulfonyl-n-phenylhydrazones . Synth. Commun. 1989 , 19 , 39 – 48 .
  • Kobayashi , S. ; Hirabayashi , R. Highly stereoselective synthesis of homoallylic amines based on addition of allyltrichlorosilanes to benzoylhydrazones under neutral conditions . J. Am. Chem. Soc. 1999 , 121 , 6942 – 6943 .
  • Lee , T. Y. ; Chung , K. Y. Silver(1)-catalyzed facile synthesis of pyrazoles from propargyl n-sulfonylhydrazones . J. Org. Chem. 2008 , 73 , 4698 – 4701 .
  • Mundal , A. D. ; Lutz , E. K. ; Thomson , J. R. Stereoselective synthesis of dienes from n-allyhydrazones . Org. Lett. 2009 , 11 , 465 – 468 .
  • Benstead , J. D. ; Hulme , N. A. ; Mcnab , H. ; Wight , P. An efficient synthesis of substituted hydrazides . Synlett 2005 , 1571 – 1574 .
  • He , R. ; Lam , Y. An efficient solid-phase synthesis of 3-substituted and 3,3-disubstituted 1,2-dialkylpyrazolidine-3,5-diones . Org. Biomol. Chem. 2008 , 6 , 2182 – 2186 .
  • Cahhi , S. ; La Torre , F. ; Mistiti , D. N-Alkylation of tosylhydrazones through phase-transfer catalysis . Synthesis 1977 , 301 – 303 .
  • Reddy , C. R. ; Jithender , E. Hydrogen peroxide–mediated formation of heteroaryl ethers from pyridotriazol-1-yloxy heterocycles and arylboronic acids . Tetrahedron Lett. 2009 , 50 , 5633 – 6536 .
  • Keith , M. J. ; Gomez , L. Exploration of the mitsunobu reaction with tosy- and boc-hydrazones as nucleophilic agents . J. Org. Chem. 2006 , 71 , 7113 – 7116 .
  • Henry , M. P. ; Marcin , R. L. ; Mcintosh , C. M. ; Sock , M. P. ; Harris , D. G. ; Weinreb , M. S. Mitsunobu reactions of n-alkyl and n-acyl sulfonamide: An efficient route to protected amines . Tetrahedron Lett. 1989 , 30 , 5709 – 5712 .
  • Yavari , I. ; Hossanini , Z. ; Alizadeh , A. Diastereselective synthesis of meso-bisphosphonates from trialkyl(aryl) phosphites and activated acetylenes in the presence of 4-nitrophenol . Monatsh. Chem. 2006 , 137 , 1083 – 1088 .
  • Islam , A. M. ; Abdel-Halim , A. M. ; Salama , M. A. Synthesis of some naphthalene-sulphonohydrazides and related compounds of potential biological activity . Egypt. J. Chem. 1987 , 29 , 405 – 409 .

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