Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 9
485
Views
8
CrossRef citations to date
0
Altmetric
Original Articles

Microwave-Assisted N-Cyclopropylation of Pyridinols with Cyclopropyl Boronic Acid

, , &
Pages 1341-1348 | Received 25 Oct 2010, Published online: 11 Jan 2012

REFERENCES

  • (a) Brown , H. C. ; Fletcher , R. S. ; Johannesen , R. B. I-strain as a factor in the chemistry of ring compounds . J. Am. Chem. Soc. 1951 , 73 , 213 – 221 ; (b) Roberts , J. D. ; Chambers , V. C. Small-ring compounds, VII: Physical and chemical properties of cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl derivatives . J. Am. Chem. Soc. 1951 , 73 , 5030 – 5034 .
  • Shaffer , C. L. ; Harriman , S. ; Koen , Y. M. ; Hanzlik , R. P. Formation of cyclopropanone during cytochrome P450-catalysed N-dealkylation of a cyclopropylamine . J. Am. Chem. Soc. 2002 , 124 , 8268 – 8274 .
  • Lesher , G. Y. N,N′-Heptamethylenebis(4-methoxybenzamide) . U.S. Patent 4009208, February 22, 1977 .
  • (a) Shostakovskii , S. M. ; L'vov , A. I. ; Kimel'fel'd , Y. M. Cyclopropyl aryl ethers . Izv. Akad. Nauk SSSR, Ser. Khim. 1966 , 1754, Chem. Abstr. 66, 37558; (b) Retinskii , A. A. ; Shostakovskii , S. M. ; Kositsyna , E. I. Phenyl cyclopropyl ethers in electrophilic substitution . Izv Akad. Nauk SSSR, Ser Khim. 1972 , 1778; (Chem. Abstr. 77, 151590; (c) Furukawa , J. ; Kawabata , N. ; Nishimura , J. Synthesis of cyclopropanes by the reaction of olefins with dialkylzinc and methylene iodide . Tetrahedron 1968 , 24 , 53 – 58 .
  • Cimetiere , B. ; Julia , M. Alkene cyclopropanation with sulfonium ylids . Synlett 1991 , 271 .
  • (a) Retinskii , A. A. ; Shostakovskii , S. M. Reduction of 1-alkyl(aryl)oxy-2,2-dichlorocyclopropane. Izv. Akad. Nauk SSSR, Ser. Khim. 1967, 413; Chem. Abstr. 67, 21464; (b) Retinskii , A. A. ; Tolmasova , V. P. ; Kotomanova , G. P. ; Shostakovskii , S. M. Synthesis and some conversion of gem-dihalocyclopropyl ethers. Izv. Akad. Nauk SSSR, Ser. Khim. 1968, 164; Chem. Abstr. 69, 18643.
  • Hollingworth , G. J. ; Dinnell , K. ; Dickinson , L. C. ; Elliott , J. M. ; Kulagowski , J. J. ; Swain , C. J. ; Thomson , C. G. A convenient method for the preparation of aryl cyclopropyl ethers from phenols . Tetrahedron Lett. 1999 , 40 , 2633 – 2636 .
  • (a) Kang , J. ; Kim , K. S. N-Cyclopropylation of aromatic amines . J. Chem. Soc., Chem. Commun. 1987 , 897 – 898 ; (b) Gillaspy , M. L. ; Lefker , B. A. ; Hada , W. A. ; Hoover , D. J. A simple method for the formation of cyclopropylamine: The first synthesis of tricyclopropylamine . Tetrahedron Lett. 1995 , 36 , 7399 – 7402 ; (c) Yoshida , Y. ; Umeza , K. ; Hamada , Y. ; Atsumi , N. ; Tabuchi , F. Practical synthesis of N-cyclopropylanilines via direct condensation of anilines with [(1-ethoxycyclopropyl)oxy]trimethylsilane . Synlett 2003 , 2139 – 2142 .
  • Gagnon , A. ; St-Onge , M. ; Little , K. ; Duplessis , M. ; Barabe , F. Direct N-cyclopropylation of cyclic amides and azoles Employing a cyclopropylbismuth reagent . J. Am. Chem. Soc. 2007 , 129 , 44 – 45 .
  • (a) Liang , G. B. ; Qian , X. ; Feng , D. ; Biftu , T. ; Eiermann , G. ; He , H. ; Leiting , B. ; Lyons , K. ; Petrov , A. ; Sinha-Roy , R. ; Zhang , B. ; Wu , J. ; Zhang , X. ; Thornberry , N. A. ; Weber , A. E. Optimization of 1,4-diazepan-2-one containing dipeptidyl peptidase IV inhibitors for the treatment of type 2 diabetes . Bioorg. Med. Chem. Lett. 2007 , 17 , 1903 – 1907 ; (b) Tran , T. P. ; Ellsworth , E. L. ; Stier , M. A. ; Domagala , J. M. ; Showalter , H. D. H. ; Gracheck , S. J. ; Shapiro , M. A. ; Joannides , T. E. ; Singh , R. Synthesis and structural–activity relationship of 3-hydroxyquinazoline-2,4-dione antibacterial agents . Bioorg. Med. Chem. Lett. 2004 , 14 , 4405 – 4409 .
  • Tsuritani , T. ; Strotman , N. A. ; Yamamoto , Y. ; Kawasaki , M. ; Yasuda , N. ; Mase , T. N-Cyclopropylation of indoles and cyclic amides with copper(II) reagent . Org. Lett. 2008 , 10 , 1653 – 1655 .
  • Benard , S. ; Neuville , L. ; Zhu , J. Copper-mediated N-cyclopropylation of azoles, amides, and sulfonamides by cyclopropylboronic acid . J. Org. Chem. 2008 , 73 , 6441 – 6444 .
  • Izatt , R. M. ; Bradshaw , J. S. ; Dalley , N. K. Coordination chemistry of lithium ion: A crystal and molecular structure review . Chem. Rev. 1991 , 91 , 137 – 164 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.