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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 23, 1993 - Issue 8
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Original Articles

A Facile Synthesis of 2-Imino-1-pyrrolidinealkanoic Acids

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Pages 1195-1199 | Received 05 Nov 1992, Published online: 23 Sep 2006

References

  • Lauria , F. , Vecchietti , V. and De Carneri , I. 1967 . Farmaco Ed. Sci. , 22 : 479
  • Rama Rao , K. , Nageswar , Y. V. D. , Srinivasan , T. N. and Sattur , P. B. 1988 . Synth. Commun. , 18 : 877 For a previous application of the use of sulfuryl chloride isocyanate to the synthesis of simple 2-iminoazaheterocycles, see
  • 1H NMR spectroscopy showed only one geometric isomer, presumably with the stereochemistry as indicated in 8–10.
  • Monitoring by 1H-NMR spectroscopy showed hydrolysis of the ester function to be rate determining
  • Kramarova , E. P. , Shipov , A. G. , Orlova , N. A. , Artamkina , O. B. , Belavin , I. Y. and Baukov , Y. I. 1988 . Zh. Obshch. Khim. , 58 : 1093
  • Takahata , H. , Okajima , H. and Yamazaki , T. 1980 . Chem. Pharm. Bull. , 28 : 3632
  • Gramain , J.-C. and Remuson , R. 1982 . J. Chem. Soc. Perkin Trans. I , : 2341
  • Miyano , S. , Fuji , S. , Yamashita , O. , Toraishi , N. and Sumoto , K. 1982 . J. Heterocyclic Chem. , 19 : 1465
  • Wagenknecht , J. H. , Baizer , M. M. and Chruma , J. L. 1972 . Synth. Commun. , 2 : 215 For esterification see
  • Spectroscopic data for 2: 1H NMR (90 MHz, D2O): δ 2.14(2H, pent, J7.7, 4-H), 2.95(2H, t, J7.7, 3-H), 3.72(2H, t, J7.1, 5-H), 4.0(2H, s, CH2CO2). For 3: δ 2.10(2H, pent, J7.7, 4-H), 2.50(2H, t, J6.4, CH2CO2), 2.89(2H, t, J7.7, 3-H), 3.62(2H, t, J6.4, β-H), 3.72(2H, t, J7.7, 5-H). For 4: δ 1.73–2.32(6H, m, 4-H, α-H, and β-H), 2.90(2H, t, J7.8, 3-H), 3.40(2H, t, J7.1, γ-H), 3.75(2H, t, J7.1, 5-H). HRMS For 2 (C6H10N2O2) calcd: 142.0742, found: 142.0741; For 3 (C7H12N2O2) calcd: 156.0899, found: 156.0921; For 4 (C8H14N2O2) calcd: 170.1054, found: 170.1023.

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