Collect. Czech. Chem. Commun. 2000, 65, 621-630
https://doi.org/10.1135/cccc20000621

A Facile Synthesis of Carboxamides by Dehydration Condensation Between Free Carboxylic Acids and Amines Using O,O'-Di(2-pyridyl) Thiocarbonate as a Coupling Reagent

Isamu Shiina, Katsuyuki Saitoh, Masakazu Nakano, Yoshihito Suenaga and Teruaki Mukaiyama*

Department of Applied Chemistry, Faculty of Science, Science University of Tokyo, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan

References

1a. Shiina I., Saitoh K., Fr├ęchard-Ortuno I., Mukaiyama T.: Chem. Lett. 1998, 3. <https://doi.org/10.1246/cl.1998.3>
1b. Saitoh K., Shiina I., Mukaiyama T.: Chem. Lett. 1998, 679. <https://doi.org/10.1246/cl.1998.679>
2. Mukaiyama T., Shiina I., Iwadare H., Saitoh M., Nishimura T., Ohkawa N., Sakoh H., Nishimura K., Tani Y., Hasegawa M., Yamada K., Saitoh K.: Chem. Eur. J. 1999, 5, 121. <https://doi.org/10.1002/(SICI)1521-3765(19990104)5:1<121::AID-CHEM121>3.0.CO;2-O>
3. For a review, see: Trost B. M., Fleming I. in: Comprehensive Organic Synthesis (E. Winterfeldt, Ed.), 1st ed., Vol. 6, p. 481. Pergamon Press, Oxford 1991.
4. Staab H. A.: Angew. Chem., Int. Ed. Engl. 1962, 1, 351. <https://doi.org/10.1002/anie.196203511>
5a. Sheehan J. C., Hess G. P.: J. Am. Chem. Soc. 1955, 77, 1067. <https://doi.org/10.1021/ja01609a099>
5b. Khorana H. G.: Chem. Ind. (London) 1955, 1087.
6. Yamada S., Kasai Y., Shioiri T.: Tetrahedron Lett. 1973, 1595. <https://doi.org/10.1016/S0040-4039(01)96005-8>
7. Shioiri T., Ninomiya K., Yamada S.: J. Am. Chem. Soc. 1972, 94, 6203. <https://doi.org/10.1021/ja00772a052>
8. Mukaiyama T., Matsueda R., Suzuki M.: Chem. Lett. 1970, 1901.
9. Kim S., Yi K. Y.: Tetrahedron Lett. 1985, 26, 1661. <https://doi.org/10.1016/S0040-4039(00)98578-2>
10. Kim S., Yi K. Y.: J. Org. Chem. 1986, 51, 2613. <https://doi.org/10.1021/jo00363a046>
11a. Dutta A., Morly J. S.: J. Chem. Soc. 1971, 2896.
11b. Effenberger F., Brodt W.: Chem. Ber. 1985, 118, 468. <https://doi.org/10.1002/cber.19851180209>
11c. Kim S., Lee J. I., Yi K. Y.: Bull. Chem. Soc. Jpn. 1985, 58, 3570. <https://doi.org/10.1246/bcsj.58.3570>
11d. Ghosh A. K., Duong T. D., McKee S. P.: Tetrahedron Lett. 1991, 34, 4251. <https://doi.org/10.1016/S0040-4039(00)92141-5>
11e. For the synthesis of esters: Ueno Y., Tanaka T., Imoto E.: Bull. Chem. Soc. Jpn. 1964, 37, 864. <https://doi.org/10.1246/bcsj.37.864>
11f. Carson J. F.: Synthesis 1979, 24. <https://doi.org/10.1055/s-1979-28534>
11g. Kim S., Lee J. I.: J. Org. Chem. 1984, 49, 1712. <https://doi.org/10.1021/jo00184a009>
11h. Keumi T., Shimada M., Morita T., Kitajima H.: Bull. Chem. Soc. Jpn. 1990, 63, 2252. <https://doi.org/10.1246/bcsj.63.2252>