Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 19
100
Views
7
CrossRef citations to date
0
Altmetric
Original Articles

Facile, Highly Stereoselective Synthesis of Cyclopropyl Benzoimidazoles via Cyclopropanation of Olefin with Arsonium Ylides

, , , , , , , , & show all
Pages 3471-3481 | Received 23 Oct 2008, Published online: 04 Sep 2009

REFERENCES

  • For reviews on the synthesis and application of cyclopropanes, please see (a) Lebel , H. ; Marcoux , J. F. ; Molinaro , C. ; Charette , A. B. Stereoselective cyclopropanation reactions . Chem. Rev. 2003 , 103 , 977 – 1050 ; (b) Pietruszka , J. Synthesis and properties of oligocyclopropyl-containing natural products and model compounds . Chem. Rev. 2003 , 103 , 1051 – 1070 ; (c) Reissig , H. U. ; Zimmer , R. Donor-acceptor-substituted cyclopropane derivatives and their application in organic synthesis . Chem. Rev. 2003 , 103 , 1151 – 1196 ; (d) Wessjohann , L. A. ; Brandt , W. Biosynthesis and metabolism of cyclopropane rings in natural compounds . Chem. Rev. 2003 , 103 , 1625 – 1647 ; (e) Taylor , R. E. ; Engelhardt , F. C. ; Schmitt , M. J. Biosynthetic inspirations: Cationic approaches to cyclopropane formation . Tetrahedron 2003 , 59 , 5623 – 5634 ; (f) Li , A. H. ; Dai , L. X. ; Aggarwal , V. K. Asymmetric ylide reactions: Epoxidation, cyclopropanation, aziridination, olefination, and rearrangement . Chem. Rev. 1997 , 97 , 2341 – 2372 .
  • (a) Ali , S. M. ; Tedford , C. ; Gregory , R. ; Handley , M. K. ; Yates , S. L. ; Hinth , W. W. ; Phillips , J. G. Design, synthesis, and structure–activity relationships of acetylene-based histamine H3 receptor antagonists . J. Med. Chem. 1999 , 42 , 903 – 909 ; (b) Kazuta , Y. ; Matsuda , A. ; Shuto , S. Development of versatile cis- and trans-dicarbon-substituted chiral cyclopropane units: Synthesis of (1S,2R)- and (1R,2R)-2-aminomethyl-1-(1H-imidazol-4-yl)cyclopropanes and their enantiomers as conformationally restricted . J. Org. Chem. 2002 , 67 , 1669 – 1677 ; (c) Muray , E. ; Rifé , J. ; Branchadell , V. ; Ortuňo , R. M. Stereoselective synthesis of novel types of cyclopropyl carbocyclic nucleosides containing quaternary stereogenic centers . J. Org. Chem. 2002 , 67 , 4520 – 4525 .
  • (a) Esposito , A. ; Taddel , M. The Kulinkovich reaction on lactones: A convenient approach to functionalized cyclopropanols . J. Org. Chem. 2000 , 65 , 9245 – 9248 ; (b) Rocchetti , M. T. ; Fino , V. ; Capriati , V. ; Florio , S. ; Luisi , R. Michael addition of chloroalkyloxazolines to electron-poor alkenes: Synthesis of heterosubstituted cyclopropanes . J. Org. Chem. 2003 , 68 , 1394 – 1400 ; (c) O'Shaughessy , J. ; Cunningham , D. ; Kavanagh , P. ; Leech , D. ; McArdle , P. ; Aldabbagh , F. Synthesis of benzimidazolequinone analogue of cyclopropamitosene antitumor agents . Synlett. 2004 , 13 , 2382 – 2384 ; (d) Miki , K. ; Yokoi , T. ; Nishino , F. ; Kato , Y. ; Washitake , Y. ; Ohe , K. ; Uemura , S. Catalytic cyclopropanation of alkenes via (2-furyl)carbene complexes from 1-benzoyl-cis-1-buten-3-yne with transition metal compounds . J. Org. Chem. 2004 , 69 , 1557 – 1564 .
  • de Frutos , M. P. ; Fernández , D. ; Fernández-Alvarez , E. ; Bernabé , M. Synthesis of asymmetric (E)-α-(2-phenylcyclopropyl)glycine . Tetrahedron Lett. 1991 , 32 , 541 – 542 .
  • Shimamoto , K. ; Ishida , M. ; Shinozaki , H. ; Ohfune , Y. Synthesis of four diastereomeric L-2-(carboxycyclopropyl)glycines: Conformationally constrained L-glutamate analogs . J. Org. Chem. 1991 , 56 , 4167 – 4176 .
  • Ma , D. ; Cao , Y. ; Yang , Y. ; Cheng , D. Stereochemically controlled cyclopropanation of (S)-glyceraldehyde acetonide-derived olefins: Synthesis of (2S,1′R,2′R,3′R)-2-(2′,3′-dicarboxycyclopropyl)glycine . Org. Lett. 1999 , 1 , 285 – 287 .
  • (a) Wermuth, C. G. The Practice of Medicinal Chemistry, 2nd ed.; Academic Press: San Diego, CA, USA, 2003; (b) Kalindjian , S. B. ; Buck , I. M. ; Davies , J. M. R. ; Dunstone , D. J. ; Hundson , M. L. ; Low , C. M. R. ; McDonald , I. M. ; Pether , M. J. ; Steel , K. I. M. ; Tozer , M. J. ; Vinter , J. G. Non-peptide cholecystokinin-B/gastrin receptor antagonists based on bicyclic, heteroaromatic skeletons. J. Med. Chem. 1996, 39, 1806–1815; (c) Nakane , M. ; Cowart , M. D. ; Hsieh , G. C. ; Miller , L. ; Uchic , M. E. ; Chang , R. ; Terranova , M. A. ; Donnelly-Roberts , D. L. ; Namovic , M. T. ; Miller , T. R. ; Wetter , J. M. ; Marsh , K. ; Stewart , A. O. ; Brioni , J. D. ; Moreland , R. B. 2-[4-(3,4-Dimethylphenyl)piperazin-1-ylmethyl]-1H benzoimidazole (A-381393), a selective dopamine D4 receptor antagonist. Neuropharmacology 2005, 49, 112–121; (d) Huang , S. ; Lin , R. ; Yu , Y. ; Lu , Y. ; Connolly , P. J. ; Chiu , G. ; Li , S. ; Emanuel , S. L. ; Middleton , S. A. Synthesis of 3-(1H-benzimidazol-2-yl)-5-isoquinolin-4-ylpyrazolo[1,2-b]pyridine, a potent cyclin dependent kinase 1 (CDK1) inhibitor. Bioorg. Med. Chem. Lett. 2007, 17, 1243–1245; (e) Ng , R. A. ; Lanter , J. C. ; Alford , V. C. ; Allan , G. F. ; Sbriscia , T. ; Lindeen , S. G. ; Sui , Z. Synthesis of potent and tissue-selective androgen receptor modulators (SARMs): 2-(2,2,2)-Trifluoroethyl-benzimidazole scaffold. Bioorg. Med. Chem. Lett. 2007, 17, 1784–1787; (f) Micco , I. ; Nencini , A. ; Quinn , J. ; Bothmann , H. ; Ghiron , C. ; Padova , A. ; Papini , S. Parallel synthesis of a series of potentially brain penetrant aminoalkyl benzoimidazoles. Bioorg. Med. Chem. 2008, 16, 2313–2328.
  • For reviews on arsonium ylides, see (a) Johnson, A. W. Ylide Chemistry; Academic Press: New York, 1966 ; (b) Song He , H. ; Wan Ying Chung , C. ; Yuen Sze But , T. ; Toy , P. H. Arsonium ylides in organic synthesis . Tetrahedron . 2005 , 61 , 1385 – 1405 ; (c) Huang , Y. ; Shen , Y. Arsonium ylides . Adv. Organomet. Chem. 1982 , 20 , 115 – 157 .
  • (a) Ren , Z. ; Cao , W. ; Chen , J. ; Wang , Y. ; Ding , W. A novel synthesis of 5-aryl-3-phenylpyrazole from 2-aryl-3-benzoyl-1,1-cyclopropane-dicarbonitrile and hydrazine. J. Heterocycli. Chem. 2006, 43, 495–497; (b) Ren , Z. ; Cao , W. ; Ding , W. ; Wang , Y. One-pot method for stereoselective cyclopropanation of electron deficient olefins with methyl bromoacetate and phenacyl bromide in the presence of triphenylarsine. Synthesis 2005, 2718–2722; (c) Ren , Z. ; Cao , W. ; Tong , W. ; Zhu , J. Solvent-free, one-pot synthesis of pyrano[2,3-c]pyrazole derivatives in the presence of KF·2H2O by grinding. Synth. Commun. 2005, 35, 2509–2513; (d) Ren , Z. ; Cao , W. ; Chen , J. ; Wang , Y. ; Ding , W. Stereoselective synthesis of cis-1-aryl-2-benzoyl-3,3-dicyanocyclopropanes in water. Synth. Commun. 2005, 35, 3099–3104; (e) Ren , Z. ; Cao , W. ; Ding , W. ; Shi , W. Solvent-free stereoselective synthesis of cis-1-carbomethoxy-2-aryl-3,3-dicyano-cyclopropanes by Grinding. Synth. Commun. 2004, 34, 4395–4400; (f) Cao , W. ; Ding , W. ; Chen , J. ; Chen , Y. ; Zang , Q. ; Chen , G. A highly stereoselective synthesis of 2,3,4,5-tetrasubstituted-trans-2,3-dihydrofurans. Synth. Commun. 2004, 34, 1599–1608; (g) Ren , Z. ; Cao , W. ; Ding , W. ; Wang , Y. ; Wang , L. Stereoselective synthesis of cis-1-aryl-2-benzoyl-3,3-dicyanocyclopropanes in the presence of KF·2H2O. Synth. Commun. 2004, 34, 3785–3792; (h) Zhang , H. ; Cao , W. ; Ren , Z. ; Chen , J. ; Sun , R. ; Hu , J. ; Qian , J. ; Deng , H. Simple approach to the highly stereoselective synthesis of trans-1,2-cyclopropane derivatives. Chin. J. Chem. 2007, 25, 1187–1191; (i) Ren , Z. ; Cao , W. ; Chen , J. ; Lu , Y. ; Wu , D. A novel synthesis of cyclopropyl lactam and amide from cis-2-Aryl-3-benzoyl-1,1-dicyanocyclopropane with H2O2 in the presence of NaHCO3 . J. Hetercycli. Chem. 2007, 44, 999–1002; (j) Cao , W. ; Zhang , H. ; Chen , J. ; Zhou , X. ; Shao , M. ; McMills , M. C. Stereoselective synthesis of highly substituted trans-2,3-dihydrofuran and trans-1,2-cyclopropane derivatives containing sulfonyl groups. Tetrahedron 2008, 64, 163–167; (k) Ren , Z. ; Cao , W. ; Tong , W. ; Chen , J. ; Wang , C. Highly stereoselective synthesis of cyclopropyl heterocycle via cyclopropanation of Olefin with Arsonium Salt. J. Heterocycli. Chem. 2008, 45, 85–90; (l) Ren , Z. ; Cao , W. ; Chen , J. ; Chen , Y. ; Deng , H. ; Shao , M. ; Wu , D. Highly stereoselective construction of spiro[cyclopropane-1,4′-pyrazolin-5′-one] with alkene and arsonium ylide. Tetrahedron 2008, 64, 5156–5161; (m) Cao , W. ; Zhang , H. ; Chen , J. ; Deng , H. ; Shao , M. ; Lu , L. ; Qian , J. ; Zhu , Y. A facile preparation of trans-1,2-cyclopropanes containing p-trifluoromethylphenyl group and its application to the construction of pyrazole and cyclopropane ring fused pyridazinone derivatives. Tetrahedron 2008, 64, 6670–6674; (n) Ren , Z. ; Cao , W. ; Tong , W. ; Chen , J. ; Deng , H. ; Wu , D. Triphenylarsine-catalyzed cyclopropanation: Highly stereoselective synthesis of trans-2,3-dihydro-spiro[cyclopropane-1,2′-indan-1′,3′-dione] from alkene and phenacyl bromide. Synth. Commun. 2008, 38, 2200–2214; (o) Ren , Z. ; Cao , W. ; Lu , Y. ; Wang , Y. ; Wang , S. Ring-expansion reaction of cyclopropane: A novel process for synthesis of bicyclic dicarboximides from cyclopropyldicarboximides and carbon nucleophile. Synth. Commun. 2008, 38, 2215–2226; (p) Chen , Y. ; Cao , W. ; Yuan , M. ; Wang , H. ; Ding , W. ; Xu , X. Study on the reaction of electron-deficient cyclopropane derivatives with aromatic amines. Synth. Commun. 2008, 38, 3346–3353; (q) Wu , X. ; Cao , W. ; Zhang , H. ; Chen , J. ; Jiang , H. ; Deng , H. ; Shao , M. ; Zhang , J. ; Chen , H. Highly stereoselective synthesis of β, γ-disubstituted and α, β, γ-trisubstituted butyrolactones. Tetrahedron 2008, 64, 10331–10338.

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.