The Synthesis of Amidine Acetals as Intermediates for the Preparation of Naturally Occurring Cyclic Amidine Antibiotics

References

• Okuyama , A. , Kondo , S. , Ikeda , T. , Miura , K. , Hamada , M. and Umezawa , H. 1979 . J. Antibiot. , 32 : 768
   PubMed Web of Science ®Google Scholar
• Data provided by the National Cancer Institute for NSC No. 334380.
   Google Scholar
• Hori , M. , Naito , K. , Sakato , N. , Vehara , Y. and Umezawa , H. 1984 . J. Antibiot. , 37 : 260
   PubMed Web of Science ®Google Scholar
• Dolak , L. A. and DeBoer , C. 1979 . J. Antibiot , 32 : 83
   PubMed Web of Science ®Google Scholar
• Nakamura , H. , Iitaka , Y. and Umezawa , H. 1979 . J. Antibiot. , 32 : 765
   PubMed Web of Science ®Google Scholar
• Horiuchi , Y. , Kondo , S. , Ikeda , T. , Miura , K. , Hamada , M. , Takeuchi , T and Umezawa , H. 1979 . J. Antibiot. , 32 : 762
   PubMed Web of Science ®Google Scholar
• Wiedhopf , R. M. , Trumbull , E. R. and Cole , J. R. 1973 . J. Pharm. Sci. , 62 : 1206
   PubMed Web of Science ®Google Scholar
• Yakushijin , K. , Kuzoka , M. , Ito , Y. , Suzuki , R. and Furukawa , H. 1980 . Heterocycles , 14 : 1073
   Web of Science ®Google Scholar
• Nagasaka , T. , Esumi , S. , Ozawa , N. , Kosugi , Y. and Hamaguchi , F. 1981 . Heterocycles , 16 : 1987
   Web of Science ®Google Scholar
• Wade , P. A. and Hinney , H. R. 1979 . J. Am. Chem. Soc. , 101 : 1319
   Web of Science ®Google Scholar
• Wade , P. A. 1978 . J. Org. Chem. , 43 : 2020
   Web of Science ®Google Scholar
• The preparation of (phenylsulfonyl)nitromethane was found to proceed much more smoothly when sodium hydride (0.9 equiv in anhydrous DMF, 0 °C, argon) was used instead of the sodium methoxide employed by Wade6b.
   Google Scholar
• Wade , P. A. , Hinney , H. R. , Amin , N. V. , Vail , P. D. , Morrow , S. D. , Hardinger , S. A. and Saft , M. S. 1981 . J. Org. Chem. , 46 : 765
   Web of Science ®Google Scholar
• The yield in the cycloaddition step is very dependent upon rapid, efficient stirring.
   Google Scholar
• Zeilstra , J. J. and Engberts , J. B. F. N. 1973 . Recl. Trav. Chim. Pays-Bas , 93 : 11
   Google Scholar
• Kelly , J. L. , McLean , E. W. and Willard , K. F. 1977 . J., Heterocycl. Chem. , 14 : 1415
   Web of Science ®Google Scholar
• Wade , P. A. and Pillay , M. K. 1981 . J. Org. Chem. , 46 : 5425
   Web of Science ®Google Scholar
• Isoxazoline spectroscopic data: 3 (a colorless liquid), 1H-NMR (CDCl3/TMS) δ 7.99 (dd, J = 7 Hz, J = 2 Hz, 2 H), 7.8–7.5 (m, 3 H), 4.81 (m, 1 H), 4.31 (d, J = 5 Hz, 1 H), 3.38 (s. 3 H), 3.34 (s, 3 H), 3.25 (d, J = 3 Hz, 2 H); 3, IR (neat) 3069, 2992, 2942, 2837, 1582, 1449, 1336, 1294, 1167, 1124, 1075, 920, 723. 688 cm−1; 4 (a colorless oil), 1H-NMR (CCl4/TMS) δ 5.38 (br m, 1 NH), 4.28 (m, 2 H), 3.37 (s, 6 H), 2.94 (d, J = 7 Hz, 2 H), 2.76 (d, J=5 Hz, 3 H); 5, (a colorless oil) 1H-NMR (CDCl3J/TMS) δ 4.51 (dt, J = 8 Hz, J = 5 Hz, 1 H), 4.27 (d, J = 5 Hz, 1 H), 3.78 (s, 3 H), 3.40 (s, 3 H), 3.37 (s, 3 H), 2.88 (d, J = 8 Hz, 2 H).
   Google Scholar
• The amidine 6 had: 1H-NMR (CDCl3/TMS + D2 O) δ 4.36 (m, 2 H), 3.43 (s, 6 H), 2.95 (d, J = 8 Hz, 2 H), 2.80 (s, 3 H); IR (neat) 3323, 3090, 3041, 3034, 2992, 2942, 2907, 2837, 1653, 1611, 1547, 1477, 1449, 1413, 1378, 1301, 1188, 1132, 1068, 976 cm−1.
   Google Scholar
• Nishimura , O. and Fujino , M. 1976 . Chem. Pharm. Bull. , 24 : 1568
   Web of Science ®Google Scholar
• Harmon , R. E. , Ham , E. A. , Bolhofer , A. and Brink , N. G. 1958 . J. Am. Chem. Soc. , 80 : 5173
   Web of Science ®Google Scholar
• Motoki , S. , Satsumabayashi , S. and Masuda , T. 1966 . Bull. Chem. Soc. Japan , 39 : 1539
   Google Scholar
• Schaefer , F. C. and Peters , G. A. 1961 . J. Org. Chem. , 26 : 412
   Web of Science ®Google Scholar
• Trost , B. M. , Shibatu , T. and Martin , S. J. 1982 . J. Am. Chem. Soc. , 104 : 3228
   Web of Science ®Google Scholar