Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 24, 1994 - Issue 12
55
Views
11
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis and Mercury (II) Trifluoroacetate Mediated Cyclization of N-Aryl -Allenylmethyl Carbamide

&
Pages 1691-1700 | Received 11 Nov 1993, Published online: 23 Sep 2006

References

  • Balakumar , A. , Janardhanam , S. and Rajagopalan , K. 1993 . J. Org. Chem. , 58 : 5482
  • Janardhanam , S. , Devan , B. and Rajagopalan , K. 1993 . Tetrahedron Lett , : 6761
  • Huche , M. and Cresson , P. 1974 . Bull. Soc. Chim. France , : 2040
  • Sleeman , M. J. and Meehan , G. V. 1989 . Tetrahedron Lett. , 30 : 3345
  • Dulcere , J. P. and Crandall , J. K. 1990 . J. Chem. Soc. Chem. Comm. , : 561
  • Ochiai , M. , Ito , T. , Takaoka , Y. and Masaki , Y. 1991 . J. Am. Chem. Soc. , 113 : 1319
  • Rhoads , S. J. and Raulins , N. R. 1974 . Org. React. , 22 : 1
  • Bennett , G. B. 1977 . Synthesis , : 589
  • Lutz. , R. P. 1984 . Chem. Rev. , 84 : 205
  • Przheval'skii , N. M. and Grandberg , I. I. 1987 . Russ. Chem. Rev. , 56 : 477
  • Barmettler , P. and Hansen , H. J. 1990 . Helv. Chim. Acta , 73 : 1515
  • Chen , Y. , Huesmann , P. L. and Mariano , P. S. 1983 . Tetrahedron. Lett. , 24 : 1021
  • Koneko , K. , Katayama , H. , Saito , Y. , Fujita , N. and Kato , A. 1986 . J. Chem. Soc. Chem. Comm. , : 1308
  • Katayama , H. 1978 . Chem. Pharm. Bull. , 26 : 2027
  • Majumdar , K. C. , Chattopadhyay , S. K. and Khan , A. T. 1989 . J. Chem. Soc., Perkin Trans. 1 , : 1285
  • Beholz , L. G. and Stille , J. R. 1993 . J. Org. Chem. , 58 : 5095
  • Elliot , M. and James , N. F. J. Chem. Soc. ,
  • 1967 . 1780
  • Schmid , M. , Hansen , H. J. and Schmid , H. 1973 . Helv. Chim. Acta , 56 : 104
  • Balasubramanian , T. and Balasubramanian , K. K. 1991 . Tetrahedron Lett. , 32 : 6641
  • Bates , D. K. and Jones , M. C. 1978 . J. Org. Chem. , 43 : 3775
  • Bluthe , N. , Malacriae , M. and Gore , J. 1984 . Tetrahedron , 40 : 3277
  • Spectral data for selected compounds. 2a : IR(CC14, Umax' cm−1); 3300 (─C═CH), 2220 (─C═N), 1590 (Aromatic C=C). 1H NMR (CDC13, 400 MHz) δ: 7.22–7.18 (m,2H, Ar-H), 6.98–6.94 (m,3H, Ar─H), 4.14 (d,2H, ─N─CH2),. 2.41 (t,1H,─C─CH). 13C NMR (CDC13, 100.6 MHz) δ 138.23 (s), 129.09 (d), 123.5(d), 115.31 (d), 112.15(s), 75.46(d), 75.33(s), 39.23 (t). 2b: 1H NMR (CDC13, 300 MHz), 7.13 (ABq, 4H, Ar─H), 4.34 (d, 2H, ─NCH2, 2.55 (t, 1H ─C═CH), 2.34 (s, 3H, Ar─CH3). 4a: IR (CC14, νmax cm−1); 2220, 1950 1590 1490, 1210, 1180. 1H NMR (CDC13, 400 MHz) δ; 7.2 (m, 2H, Ar─H), 6.96 (m, 3H, Ar─H), 5.15 (m, 1H,°C═), 4.76 (m, 2H,=CH2), 4.03 (m, 2H, ─NCH2). 13C NMR (CDC13, 100.6 MHz) δ; 209.179(s), 139.113(s), 129.155 (d), 123.159(d), 115.479(d), 112.883(s), 84.423 (d), 77.577 (t), 48.084 (t). 4b: IR (CHC13, νmax, cm−1): 2220, 1950, 1H NMR (CDC13, 300 MHz) δ; 7.11 (ABq, 4H, Ar─H), 5.21–5.30 (m, 1HH,═) 4.86–4.9 (m, 2HH,═) 4.11–4.15 (m, 2H, ─N─CH2), 2.28 (S, 3H, Ar─CH3). 13C─NMR (75.4 MHz, CDC13); 209.2(s), 136.7(s), 132.8(s), 129.72(d), 115.7(d), 113.3(s), 84.55 (d), 77.51(t), 48.39 (t), 20.1(q). 5a: IR (CHC13, νmax cm−1), 3020, 2020, 1600, 1490, 1320, 1280, 1NMR (CDC13, 90 MHz) δ; 5.48 (s, 1H, Hb), 4.92 (s, 1H,H2), 3.72 (t, 2H, ─ N─CH2), 2.65 (t, 2H, allylic CH2), 7. 3 - 6.9(m,4H,Ar ─H). 5b: IR (CHC13, νmax cm−1), 3020, 2020, 1595. 1H NMR (CC14/TMS, 90 MHz) δ; 7.3 (s, 1H, Ar─H), 7.0 (s, 2H, Ar─H), 5.4 (s, 1H,Hb), 4.8 (s, 1H,H2), 3.7 (t, 2H, ─N─CH2, 2.6 (t, 2H, Allylic ─ CH2), 2.0 (s, 3H, Ar─CH3)
  • Bowden , B. F. , Picker , K. , Ritchie , E. and Taylor , W. C. 1975 . Aust. J. Chem. , 28 : 2681
  • Bowden , B. F. , Freeman , H. C. and Jones , R. D.G. 1976 . J. Chem. Soc., Perkin Trans. 2 , : 658

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.