Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 24
421
Views
9
CrossRef citations to date
0
Altmetric
Original Articles

A Novel and Efficient Reaction of Imidazolidin-2-one and N-Acylbenzotriazoles: A Facile Synthesis of 1-Acylimidazolidin-2-one

, , &
Pages 3669-3677 | Received 16 May 2008, Published online: 09 Nov 2010

REFERENCES

  • (a) Kohn , H. Model Studies on the Mechanism of Biotin Dependent Carboxylations . J. Am. Chem. Soc. 1976 , 98 , 3690 – 3694 ; (b) Pratt , R. F. ; Bruice , T. C. Reactions of S-acylisothioureas.II. Effects of structure and stereochemistry on the rates of hydrolysis, thiol elimination, and S to N acyl migration in acylic systems . J. Am. Chem. Soc. 1972 , 94 , 2823 – 2837 ; (c) Kohn , H. ; Kohn , B. A. ; Steenberg , M. L. ; Buckley , J. P. Syntheses and pharmacological activity of substituted imidazolidinethiones and thioimidazolines . J. Med. Chem. 1977 , 20 , 158 – 160 ; (d) Marx , J. L. Cancer immunotherapy: Focus on the drug levamisole . Science 1976 , 191 , 57 .
  • (a) Euis , C. J. Mezlocillin and azlocillin: An evaluation of two new β-lactam antibiotics . Antimicrob Chemother. 1979 , 5 , 517 – 525 ; (b) Baker , M. J. Infection 1979 , 7 , 67 .
  • Gudzenko , V. I. ; Salov , B. V. Method for preparing 1-acetyl-2-imidazolidone . Patent, Ru 2237662 , 2004 .
  • Kohn , H. ; Cravey , M. J. Syntheses and spectral properties of substituted imidazolidones and imidazolines . J. Org. Chem. 1977 , 42 , 941 – 948 .
  • Su , W. K. ; Yin , X. J. ; Lu , Y. J. Synthesis of N-Actyl-Imidazolidone-2 . J. Zhejiang Univ of Technol (China) 1995 , 23 , 136 – 140 .
  • Katritzky , A. R. ; Suzuki , K. ; Wang , Z. Acylbenzotriazoles as advantageous N-, C-, S-, and O-acylation agents . Synlett 2005 , 1656 – 1665 .
  • (a) Katritzky , A. R. ; He , H. Y. ; Suzuki , K. N-Acylbenzotriazoles: Neutral acylating reagents for the preparation of primary, secondary, and tertiary amides. J. Org. Chem. 2000, 65, 8210–8213; (b) Katritzky , A. R. ; Zhang , Y. ; Singh , S. K. Efficient conversion of carboxylic acids into N-acylbenzotriazoles. Synthesis 2003, 2795–2798.
  • Katritzky , A. R. ; Pastor , A. ; Voronkov , M. V. An efficient general synthesis of 1-(benzotriazol-1-yl)alkyl esters . J. Heterocycl. Chem. 1999 , 36 , 777 – 782 .
  • Zou , X. ; Wang , X. ; Cheng , C. ; Kong , L. ; Mao , H. Highly regioselective Friedel–Crafts alkylation of indoles with α,β-unsaturated N-acylbenzotriazoles . Tetrahedron Lett. 2006 , 47 , 3767 – 3771 .
  • Katritzky , A. R. ; Suzuki , K. ; Singh , S. K. ; He , H.-Y. Regiospecific C-acylation of pyrroles and indoles using N-acylbenzotriazoles . J. Org. Chem. 2003 , 68 , 5720 – 5723 .
  • (a) Katritzky , A. R. ; Abdel-Fattah , A. A. A. ; Wang , M. Expedient acylations of primary and secondary alkyl cyanides to α-substituted β-ketonitriles . J. Org. Chem. 2003 , 68 , 4932 – 4934 ; (b) Katritzky , A. R. ; Pastor , A. Synthesis of β-dicarbonyl compounds using 1-acylbenzotriazoles as regioselective C-acylating reagents . J. Org. Chem. 2000 , 65 , 3679 – 3682 ; (c) Katritzky , A. R. ; Meher , N. K. ; Singh , S. K. γ,δ-Unsaturated β-diketones by acylation of ketones . J. Org. Chem. 2005 , 70 , 7792 – 7794 ; (d) Katritzky , A. R. ; Abdel-Fattah , A. A. A. ; Gromova , A. V. ; Witek , R. ; Steel , P. J. α-Nitro ketone synthesis using N-acylbenzotriazoles . J. Org. Chem. 2005 , 70 , 9211 – 9214 ; (e) Katritzky , A. R. ; Jiang , R. ; Suzuki , K. N-Tfa- and N-Fmoc-(α-aminoacyl)benzotriazoles as chiral C-acylating reagents under Friedel-Crafts reaction conditions . J. Org. Chem. 2005 , 70 , 4993 – 5000 ; (f) Katritzky , A. R. ; Angrish , P. ; Hür , D. ; Suzuki , K. N-(Cbz- and fmoc-α-aminoacyl)benzotriazoles: Stable derivatives enabling peptide coupling of Tyr, Trp, Cys, Met, and Gln with free amino acids in aqueous media with complete retention of chirality . Synthesis 2005 , 397 – 402 .
  • Katritzky , A. R. ; Hoffmann , S. ; Suzuki , K. N-Acylation of sulfonamides using N-acylbenzotriazoles . ARKIVOC 2004 , xii , 14 – 22 .
  • (a) Katritzky , A. R. ; Angrish , P. ; Suzuki , K. The efficient preparation of Di- and Tripeptides by coupling N-(Cbz- or Fmoc-α -aminoacyl)benzotriazoles with unprotected amino acids . Synthesis 2006 , 411 – 424 ; (b) Katritzky , A. R. ; Tao , H. ; Jiang , R. ; Suzuki , K. ; Kirichenko , K. Novel Syntheses of chiral β- and γ-amino acid derivatives utilizing N-protected(aminoacyl)benzotriazoles from aspartic and glutamic acids . J. Org. Chem. 2007 , 72 , 407 – 414 ; (c) Katritzky , A. R. ; Singh , S. K. ; Akhmedova , R. ; Cai , C. ; Bobrov , S. Efficient synthesis of 1,3-benzodixin-4-one and benzoxazine-2,4-diones . ARKIVOC 2007 , vi , 6 – 13 ; (d) Katritzky , A. R. ; Shestopalov , A. A. ; Suzuki , K. A new convenient preparation of thiol esters utilizing N-acylbenzotriazoles . Synthesis 2004 , 1806 – 1813 ; (e) Singh , K. N. ; Kaur , A. Facile and chemoselective reduction of carboxylic acids into alcohols via sodium borohydride reduction of N-Acylbenzotriazoles . Synth. Commun. 2005 , 35 , 2935 – 2937 ; (f) Katritzky , A. R. ; Angrish , P. Convenient and efficient preparation of N-Protected(a-Aminoacyl)oxy-substituted terpenes and alkanes . Synthesis 2006 , 4135 – 4142 ; (g) Wang , X. ; Zou , X. ; Li , J. ; Hu , Q. Efficient syntheses of β-amino-N-acylbenzotriazoles and cinnamides through regioselective 1,4- or 1,2-addition of amines to N-cinnamoylbenzotriazoles . Synlett 2005 , 3042 – 3046 .
  • Katritzky , A. R. ; Khelashvili , L. ; Mohapatra , P. P. ; Steel , P. J. Efficient N-Aroylation of substituted indoles with N-Aroylbenzotriazoles . Synthesis 2007 , 3673 – 3677 .
  • May , Hans-Joachim ; Konig , Horst. Neue 1-acyl-2-imidazoline und Verfahren zu ihrer Herstellung. Patent, Ger Offen DE 2652004 A1 , 1978 .

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.