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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 3
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Original Articles

Novel Procedure for Highly Stereoselective Synthesis of Bicyclic Cyclopropane‐lactam with cis‐2‐Aryl‐1‐benzoyl‐3,3‐dicyanocyclopropane and 2‐Cyanomethyl‐1,3‐benzothiazole in Water

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Pages 391-398 | Received 06 Jul 2006, Published online: 06 Feb 2007

References

  • Wong , H. N. C. , Hon , M.‐Y. , Tse , C.‐W. , Yip , Y.‐C. , Tanko , J. and Hudicky , T. 1989 . Use of cyclopropanes and their derivatives in organic synthesis . Chem. Rev. , 89 : 165 – 198 .
  • de Meijere , A. 2000 . Small Ring Compounds in Organic Synthesis VI Edited by: de Meijere , A. Vol. 207 , Berlin : Springer .
  • Greatrex , B. W. , Taylor , D. K. and Tiekink , R. T. 2002 . An anioic C3–C5 ring expansion of β‐ketocyclopropanes to cyclopentenols . Org. Lett. , 4 : 221 – 224 .
  • Bertozzl , F. , Gustsfsson , M. and Olsson , R. 2002 . One‐pot three‐component reaction for the synthesis of α‐(aminoethyl)‐α,β‐enones . Org. Lett. , 4 : 4333 – 4336 .
  • Kung , H. F. , Lee , C.‐W. , Zhuang , Z.‐P. , Kung , M.‐P. , Hou , C. and Plössl , K. 2001 . Novel stilbenes as probes for amyloid plaques . J. Am. Chem. Soc. , 123 : 12740 – 12741 .
  • Hutchinson , I. , Jennings , S. A. , Vishnucajjala , B. R. , Westwell , A. D. , Westwell , A. D. and Stevens , F. G. M. 2002 . Antitumor benzothiazloes, 161: Synthesis and pharmaceutical properties of antitumor 2‐(4‐aminophenyl)benzothiazole amino acid prodrugs . J. Med. Chem. , 45 : 744 – 747 .
  • Barchéchath , S. D. , Tawatao , R. I. , Corr , M. , Carson , D. A. and Cottam , H. B. 2005 . Inhibitors of apoptosis in lymphocytes: Synthesis and biological evaluation of compounds related to pifithrin‐α . J. Med. Chem. , 48 : 6409 – 6422 .
  • Ren , Z.‐J. , Cao , W.‐G. , Ding , W.‐Y. and Wang , Y. 2005 . One‐pot method for stereoselective cyclopropanation of electron deficient olefins with methyl bromoacetate and phenacyl bromide in the presence of triphenylarsine . Synthesis , : 2718 – 2722 .
  • Cao , W.‐G. , Ding , W.‐Y. , Chen , Y.‐L. and Gao , J. S. 2000 . Study on the reaction of cis‐1‐acetyl‐2‐aryl‐6,6‐dimethyl‐5,7‐dioxo‐spiro‐[2,5]‐4,8‐octadiones with methanol . Synth. Commun. , 30 : 4531 – 4541 .
  • Chen , Y.‐L. , Ding , W.‐Y. , Cao , W.‐G. and Lu , C. 2001 . The stereoselective synthesis of n‐aryl‐trans, trans‐α‐carboxyl‐β‐methoxycarbonyl‐γ‐aryl‐γ‐butyrolactams . Synth. Commun. , 31 : 3107 – 3112 .
  • Li , C. J. 1993 . Organic reaction in aqueous media with a focus on carbon–carbon bond formation . Chem. Rev. , 93 : 2023 – 2035 .
  • Li , C.‐J. and Chan , T.‐H. 1997 . “ Organic Reactions in Aqueous Media ” . New York : Wiley .
  • Grieco , P. A. 1998 . Organic Synthesis in Water Edited by: Grieco , P. A. London : Blackie Academic & Professional .
  • Wang , S. , Ren , Z. , Cao , W. and Tong , W. 2001 . The Knoevenagel condensation of aromatic aldehydes with malononitrile or ethyl cyanoacetate in the presence of CTMAB in water . Synth. Commun. , 31 : 673 – 677 .
  • Ren , Z. , Cao , W. , Tong , W. and Jin , X. 2002 . The knoevenagel condensation of aldehydes with cyclic active methylene compounds in water . Synth. Commun. , 32 : 1947 – 1952 .
  • Ren , Z. , Cao , W. , Chen , J. , Wang , Y. and Ding , W. 2005 . Stereoselective synthesis of cis‐1‐Aryl‐2‐benzoyl‐3,3‐dicyanocyclopropanes in Water . Synth. Commun. , 35 : 3099 – 3104 .
  • Saito , K. , Kambe , S. and Nakano , Y. 1983 . Synthetic studies using α,β‐unsaturated nirtriles: A convenient preparation of 1,3‐benzothiazole derivatives . Synthesis , : 210 – 212 .
  • Zhong , R. , Mamai , A. and Madalengoitia , J. S. 1999 . Cyclopropanation reaction pyroglutamic acid‐derived synthons with akylidene transfer reagents . J. Org. Chem. , 64 : 547 – 555 .
  • Gunther , H. 1980 . NMR Spectroscopy 108 – 384 . New York : Wiley .

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