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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 22
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Original Articles

Convenient Methodology for the Synthesis of Trialkylhydrazines

, &
Pages 3958-3972 | Received 05 Sep 2008, Published online: 16 Oct 2009

REFERENCES

  • Ragnarsson , U. Synthetic methodology for alkyl substituted hydrazines . Chem. Soc. Rev. 2001 , 30 , 205 – 213
  • Othmer , D. F. ; Kirk , R. E. Hydrazine and its derivatives ; In Encyclopedia of Chemical Technology; , 4th ed .; Wiley : New York , 1995 ; vol. 13 .
  • Bredihhin , A. ; Groth , U. M. ; Mäeorg , U. Efficient methodology for selective alkylation of hydrazine derivatives . Org. Lett. 2007 , 9 , 1097 – 1099 .
  • Zhang , R. ; Durkin , J. P. ; Windsor , W. T. Azapeptides as inhibitors of the hepatitis C virus NS3 serine protease . Bioorg. Med. Chem. Lett. 2002 , 12 , 1005 – 1008 .
  • Cherney , M. M. ; Huitema , C. ; Liu , J. ; James , K. E. ; Powers , J. C. ; Eltis , L. D. ; James , M. N. Crystal structures of the main peptidase from the SARS coronavirus inhibited by a substrate-like aza-peptide epoxide . J. Mol. Biol. 2005 , 354 , 1137 – 1151 .
  • Huddleston , P. R. ; Coutts , I. G. C. Comprehensive Organic Functional Group Transformations ; A. R. Katriztky , O. Meth-Cohn , C. W. Rees (Eds.) Pergamon/Elsevier : Oxford , 1995 ; vol. 2 , pp. 371 – 383 .
  • Greene , T. W. ; Wuts , P. G. M. Protective Groups in Organic Synthesis; 3rd. ed ; Wiley-Interscience : New York , 1999; ch. 7.
  • Brosse , N. ; Pinto , M. F. ; Jamart-Gregoire , B. New synthesis of 1,1-substituted hydrazines by alkylation of N-acyl- or N-alkyloxycarbonylaminophthalimide using the Mitsunobu protocol . J. Org. Chem. 2000 , 65 , 4370 – 4374 .
  • Brosse , N. ; Pinto , M. F. ; Bodigue , J. ; Jamart-Gregoire , B. A new synthetic route to protected α-hydrazinoesters in high optical purity using the Mitsunobu protocol . J. Org. Chem. 2001 , 66 , 869 – 2873 .
  • Vazquez , A. ; Goldberg , R. ; Nudelman , N. S. Organolithiums as useful synthetic intermediates for tandem reactions ; In The Chemistry of Functional Groups: Lithium Chemistry ; S. Patai , Z. Rappaport (Eds.); Wiley , Chichester , UK , 2005 ; ch. 2, pp. 63–137 .
  • García , G.V. ; Nudelman , N. S. Tandem reactions involving organolithium reagents; A review . Org. Prep. Proc. Int. 2003 , 35 , 445 – 500 .
  • Polshettiwar , V. ; Varma , R. S. Polystyrene sulfonic acid catalyzed greener synthesis of hydrazones in aqueous medium using microwaves . Tetrahedron Lett. 2007 , 48 , 5649 – 5652
  • Nicolau , K. C. ; Yue , E. W. ; Oshima , T. New roads to molecular complexity ; In The New Chemistry ; N. Hall (Ed.); Cambridge University Press : Cambridge, UK , 2000 ; p. 178 .
  • Waldmann , H. Domino reaction ; In Organic Synthesis Highlight II ; H. Waldmann (Ed.); VCH : Weinheim , 1995 ; p. 193 .
  • Tietze , L. F. Domino reactions in organic synthesis . Chem. Rev. 1996 , 96 , 115 .
  • Nudelman , N. S. ; Bonatti , A. E. A highly convenient new methodology for the synthesis of N-nitrosamines from lithium amides . Synlett 2000 , 1825 – 1827 .
  • (a) Abnet , C. C. Carcinogenic food contaminants . Cancer Investigat. 2007 , 25 , 189 – 196 . (b) Guza , R. ; Rajesh , M. ; Fang , Q. ; Pegg , A. E. ; Tretyakova , N. Kinetics of O6-methyl-2′-deoxyguanosine repair by O 6-alkylguanine DNA alkyltransferase within K-ras gene-derived DNA sequences . Chem. Res. Toxicol. 2006 , 19 , 531 – 538 .
  • Loeber , R. ; Rajesh , M. ; Fang , Q. ; Pegg , A.E. ; Tretyakova , N. Cross-linking of the human DNA repair protein O6-alkylguanine DNA alkyltransferase to DNA in the presence of 1,2,3,4-diepoxybutane . Chem. Res. Toxicol. 2006 , 19 ( 5 ), 645 – 654 .
  • Ikeda , M. ; Masumura , K. ; Sakamoto , Y. ; Wang , B. ; Nenoi , M. ; Sakuma , K. ; Hayata , I. ; Nohmi , T. Combined genotoxic effects of radiation and a tobacco-specific nitrosamine in the lung of gpt delta transgenic mice . Mutat. Res. 2007 , 626 , 15 – 25 .
  • Loft , S. ; Svoboda , P. ; Kasai , H. ; Tjonneland , A. ; Moller , P. ; Sorensen , M. ; Overbad , K. ; Autrup , H. ; Raaschou-Nielsen , O. Prospective study of urinary excretion of 7-methylguanine and the risk of lung cancer: Effect modification by mu class glutathione-S-transferases . Int. J. Cancer 2007 , 121 , 1579 – 1584 .
  • Bonde , P. ; Gao , D. ; Chen , L. ; Miyashita , T. ; Montgomery , E. ; Harmon , J. W. ; Wei , C. Duodenal reflux leads to down regulation of DNA mismatch repair pathway in an animal model of esophageal cancer . Ann. Thorac. Surg. 2007 , 83 , 433 – 440 .
  • Krul , C. ; Zeilmaker , M. J. ; Schothorst , R. C. ; Havenaar , R. Intragastric formation and modulation of N-nitrosodimethylamine in a dynamic in vitro gastrointestinal model under human physiological conditions. Food Chem. Toxicol. 2004, 42, 51–63.
  • (a) Zou , X. N. ; Lu , S. H. ; Liu , B. Volatile N-nitrosamines and their precursors in Chinese salted fish-–A possible etological factor for NPC in China . Int. J. Cancer 1994 , 59 , 155 – 158 . (b) Lijinsky , W. N-Nitroso compounds in the diet . Mutat. Res. 1999 , 443 , 129 – 138 .
  • Breuil-Desvergnes , V. ; Goré , J. Reaction of the lithio-derivative of methoxyallene with hydrazones, part 1: Synthesis and transformation of a-allenyl hydrazines . Tetrahedron 2001 , 57 , 1939 – 1950 .
  • Adler , M. ; Marsch , M. ; Nudelman , N. S. ; Boche , G. [(Ph)2(NMe2)C(OLi)·THF]2: Crystal structure of the tetrahedral intermediate formed in the reaction of N,N-dimethylbenzamide and phenyllithium . Angew. Chem, Int. Ed. Engl. 1999 , 38 , 1261 – 1263 .
  • Nudelman , N. S. ; Schulz , H. ; García Liñares , G. ; Bonatti , A. E. Further insights into the chemistry of acyllithium compounds R2NC(O)Li: Characterization of an amide (R2NLi) adduct (R2NCHNR2(OLi)) to a formamide (R2NC(O)H) . Organometallics 1998 , 17 , 146 – 150 .
  • Nudelman , N. S. ; García Liñares , G. New insights into the chemistry of lithium carbamoyls: Characterization of an adduct (R2NC(O)CLi(OLi)NR2) . J. Org. Chem. 2000 , 65 , 1629 – 1635 .
  • Michejda , C. J. ; Schluenz , R. W. Reactions of N-nitrosamines with Grignard and lithium reagents . J. Org. Chem. 1973 , 38 , 2412 – 2415 .
  • Farina , P. R. ; Tieckelmann , H. Some reactions of organolithium compounds with nitrosamines . J. Org. Chem. 1973 , 38 , 4259 – 4263 .
  • Farina , P. R. ; Tieckelmann , H. Reactions of Grignard reagents with nitrosamines . J. Org. Chem. 1975 , 40 , 1070 – 1074 .
  • Perdicchia , D. ; Licandro , E. ; Mairorana , S. ; Baldoli , C. A new “one-pot” synthesis of hydrazides by reduction of hydrazones . Tetrahedron 2003 , 59 , 7733 .
  • Rajamäki , M. ; Vigroux , A. ; Chahoua , L. ; Fishbein , J. C. N-Nitrosiminium ions are ambident electrophiles . J. Org. Chem. 1995 , 60 , 2324 – 2325 .
  • Vázquez , A. J. ; Nudelman , N. S. The unexpected effects of added ligands on the addition of phenyllithium to E-cinnamaldehyde in THF . Arkivoc 2005 , 332 – 340 .
  • Vázquez , A. J. ; Nudelman , N. S. Complex intermediates in the NO insertion reactions into lithium amides . J. Phys. Org. Chem. 2006 , 19 , 748 – 751 .

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