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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 13
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Original Articles

Triton B–Mediated Mild, Convenient, and Efficient Method for the Selective Alkylation of Cyclic Secondary Amines and Thiols

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Pages 2297-2303 | Received 21 Aug 2008, Published online: 01 Jun 2009

REFERENCES

  • Mohri , K. ; Suzuki , K. ; Usui , M. ; Isobe , K. ; Tsuda , Y. A convenient synthesis of tertiary amines by alkylation of secondary amines with allyl halides in the presence of potassium hydroxide and triethyl amine . Chem. Pharm. Bull. Jpn. 1995 , 43 ( 1 ), 159 – 161 .
  • (a) Semple , G. ; Andersson , B. M. ; Chhajlani , V. ; Georgsson , J. ; Johnsson , M. J. ; Rosenquist , A. ; Swanson , L. Synthesis and biological activity of kappa opioid receptor agonists, part 2: Preparation of 3-aryl-2-pyridone analogues generated by solution and solid-phase parallel synthesis methods . Bioorg. Med. Chem. Lett. 2003 , 13 , 1141 – 1145 ; (b) Breukelman , S. P. ; Meakins , G. D. ; Roe , A. M. Preparation and some reactions of 4- and 5-aryl-4,5-dihydro pyridazin-3(2H)-ones . J. Chem. Soc., Perkin Trans. 1. 1985 , 1627 – 1635 .
  • Ottoni , O. ; Cruz , R. ; Alves , R. Efficient and simple methods for the introduction of the sulfonyl, acyl, and alkyl protecting groups on the nitrogen of indole and its derivatives . Tetrahedron. 1998 , 54 , 13915 – 13928 .
  • (a) Bogdal , D. ; Pielichowski , J. ; Jaskot , K. A number of azaheterocycles reacts remarkably fast with alkyl halides to give exclusively N-alkyl derivatives . Heterocycles. 1997 , 45 ( 4 ), 715 – 722 ; (b) Bogdal , D. ; Pielichowski , V. ; Jaskot , K. New synthesis of N-alkylation of carbazole under microwave irradiation in dry media . Synth. Commun. 1997 , 27 , 1553 – 1560 ; (c) Pawelczyk , A. ; Zaprutko , L. Microwave assisted synthesis of fragrant jasmine heterocyclic analogues . Eur. J. Med. Chem. 2006 , 41 , 586 – 591 .
  • Vinod Kumar , R. ; Seshu Kumar , K. V. S. R. ; Raja Gopal , K. Facile synthesis of 2-(substituted benzyl sulfonyl) benzothiazoles and their antimicrobial activity screening . J. Hetrocycl. Chem. 2005 , 42 ( 1 ), 153 – 156 .
  • Moore , J. L. ; Taylor , S. M. ; Vadim , A. An efficient and operationally convenient general synthesis of tertiary amines by direct alkylation of secondary amines with alkyl halides in the presence of Huenig's base . Soloshonok Arkivoc. 2005 , 287 – 292 .
  • Zhang , M. ; Moore , J. ; Flynn , D. L. ; Hanson , P. R. Development of high-load, soluble oligomeric sulfonate esters via ROM polymerization: Application to the benzylation of amines . Org. Lett. 2004 , 6 , 2657 – 2660 .
  • Morphy , J. R. ; Rankovic , Z. ; York , M. Reagent concentration effects in the REM resin solid phase synthesis of tertiaryamines . Tetrahedron. 2003 , 59 , 2137 – 2145 ; Perrence , L. ; Loupy , A. ; Delmotte , M. Microwave effects in solvent-free esters aminolysis . Tetrahedron. 2003 , 59 , 2185 – 2189 .
  • Yang , N. C. ; Finnegan , R. A. A new method for the epoxidation of α,β-unsaturated ketones . J. Am. Chem. Soc. 1958 , 80 , 5845 – 5848 ; Kamikubo, T.; Matlack, A. S. Introduction to Green Chemistry; Maseel Dekker: New York, 2001 .
  • Starks , C. Phase-transfer catalysis, I: Heterogeneous reactions involving anion transfer by quaternary ammonium and phosphonium salts. J. Am. Chem. Soc. 1971, 93, 195–199.
  • Rideout , D. C. ; Breslow , R. Hydrophobic acceleration of Diels–Alder reactions . J. Am. Chem. Soc. 1980 , 102 , 7816 – 7817 .
  • Hardcastle , I. R. ; Cockcroft , X. ; Curtin , N. J. ; E1-Murr , M. D. ; Leahy , J. J. J. ; Stockley , M. ; Golding , B. T. ; Rigoreau , L. ; Richardson , C. ; Smith , G. C. M. ; Griffin , R. J. Discovery of potent chromen-4-one inhibitors of the DNA-dependent protein kinase (DNA-PK) using a small-molecule library approach . J. Med. Chem. 2005 , 48 , 7829 – 7846 .

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