N-arylation of 1,2,4- and 1,3,4-oxadiazolones under the conditions of activitated aromatic nucleophilic substitution

Мұқаба

Дәйексөз келтіру

Толық мәтін

Ашық рұқсат Ашық рұқсат
Рұқсат жабық Рұқсат берілді
Рұқсат жабық Тек жазылушылар үшін

Аннотация

The possibilities of N -arylation of 1,2,4-oxadiazol-5(4 Н )-ones and 1,3,4-oxadiazol-2(3 Н )-ones with various electron-deficient chloro- and fluorine-substituted nitroarenes under the conditions of classical activated nucleophilic substitution were studied. A significant difference was shown in the reactivity of 1,2,4- and 1,3,4-oxadiazolones in N -arylation reactions. Methods for the synthesis of N-nitroaryl derivatives have been developed.1,2,4- and 1,3,4-oxadiazolones, providing yields of target products with sufficient purity and good yields at the level of 65-96%.

Авторлар туралы

A. Konstantinova

Pharmaceutical Technology Transfer Center, Ushinsky Yaroslavl State Pedagogical University;Russian State University named after A.N. Kosygin (Technology. Design. Art)

Email: a.konstantinova@yspu.org

A. Shetnev

Pharmaceutical Technology Transfer Center, Ushinsky Yaroslavl State Pedagogical University

Email: a.shetnev@list.ru

A. Volobueva

Saint Petersburg Pasteur Institute

M. Korsakov

Russian State University named after A.N. Kosygin (Technology. Design. Art)

Әдебиет тізімі

  1. Moser P.C., Bergis O.E., Jegham S., Lochead A., Duconseille E., Terranova J.P., Caille D., Berque-Bestel I., Lezoualc H.F., Fischmeister R., Dumuis A., Bockaert J., George P., Soubri� P., Scatton B. J. Pharmacol. Exp. Ther. 2002, 302, 731-741. doi: 10.1124/jpet.102.034249
  2. Shah S.K., He S., Guo L., Truong Q., Qi H., Du W., Lai Z., Liu J., Jian T., Hong Q., Dobbelaar P., Ye Z., Sherer E., Feng Z., Yu Y., Wong F., Samuel K., Madiera M., Karanam B.V., Reddy V.B., Mitelman S., Tong S.X., Chicchi G.G., Tsao K.L., Trusca D., Feng Y., Wu M., Shao Q., Trujillo M.E., Eiermann G.J., Li C., Pachanski M., Fernandez G., Nelson D., Bunting P., Morissette P., Volksdorf S., Kerr J., Zhang B.B., Howard A.D., Zhou Y.P., Pasternak A., Nargund R.P., Hagmann W. K. ACS Med. Chem. Lett. 2015, 6, 513-517. doi: 10.1021/ml500514w
  3. Baker W.L., White W.B. Ann. Pharmacother. 2011, 45, 1506-1515. doi: 10.1345/aph.1Q468
  4. Haffar O., Dubrovsky L., Lowe R., Berro R., Kashanchi F., Godden J., Vanpouille C., Bajorath J., Bukrinsky M. J. Virol. 2005, 79, 13028-13036. doi: 10.1128/JVI.79.20.13028-13036.2005.
  5. Ohmoto K., Okuma M., Yamamoto T., Kijima H., Sekioka T., Kitagawa K., Yamamoto S., Tanaka K., Kawabata K., Sakata A., Imawaka H., Nakai H., Toda M. Bioorg. Med. Chem. 2001, 9, 1307-1323. doi: 10.1016/s0968-0896(01)00007-4
  6. Bi F., Song D., Qin Y., Liu X., Teng Y., Zhang N., Zhang P., Zhang N., Ma S. Bioorg. Med. Chem. 2019, 27, 3179-3193. doi: 10.1016/j.bmc.2019.06.010
  7. Marvadi S.K., Krishna V.S., Sinegubova E.O., Volobueva A.S., Esaulkova Y.L., Muryleva A.A., Tentler D.G., Sriram D., Zarubaev V.V., Kantevari S. Bioorg. Med. Chem. Lett. 2019, 29, 2664-2669. doi: 10.1016/j.bmcl.2019.07.040
  8. Yue E.W., Sparks R., Polam P., Modi D., Douty B., Wayland B., Glass B., Takvorian A., Glenn J., Zhu W., Bower M., Liu X., Leffet L., Wang Q., Bowman K.J., Hansbury M.J., Wei M., Li Y., Wynn R., Burn T.C., Koblish H.K., Fridman J.S., Emm T., Scherle P.A., Metcalf B., Combs A.P. ACS Med. Chem. Lett. 2017, 8, 486-491. doi: 10.1021/acsmedchemlett.6b00391
  9. Phakhodee W., Duangkamol C., Wiriya N., Pattarawarapan M. RSC Adv. 2018, 8, 38281-38288. doi: 10.1039/C8RA08207C
  10. Zhou L., Li H., Zhang W., Wang L. Chem. Commun. 2018, 54, 4822-4825. doi: 10.1039/C8CC00124C
  11. Sauer J., Mayer K.K. Tetrahedron Lett. 1968, 9, 325-330. doi: 10.1016/s0040-4039(01)98754-4
  12. Soldatova N., Semenov A., Geyl K., Baykov S., Shetnev A., Konstantinova A., Korsakov M., Yusubov M., Postnikov P. Adv. Synth. Catal. 2021, 363, 1-12. doi: 10.1002/adsc.202100426
  13. Baykov S., Sharonova T., Shetnev A., Rozhkov S., Kalinin S., Smirnov A. Tetrahedron. 2017, 73, 945-951. doi: 10.1016/j.tet.2017.01.007
  14. Musser J.H., Brown R.E., Love B., Bailey K., Jones H., Kahen, R., Huang F., Khandwala A., Leibowitz M., Sonnino-Goldman P., Donigi-Ruzza D. J. Med. Chem. 1984, 27, 121-125. doi: 10.1021/jm00368a004
  15. Van der Linden L., Vives-Adrian L., Selisko B., Ferrer-Orta C., Liu X., Lanke K., Ulferts R., De Palma A.M., Tanchis F., Goris N., Lefebvre D., De Clercq K., Leyssen P., Lacroix C., Purstinger G., Coutard B., Canard B., Boehr D.D., Arnold J.J.,Cameron C.E., Verdaguer N., Neyts J., van Kuppeveld F.J. PLoS Pathog. 2015, 11, 1-23. doi: 10.1371/journal.ppat.1004733
  16. Hughes G., Bryce M.R. J. Mater. Chem. 2005, 15, 94-107. doi: 10.1039/B413249C

Қосымша файлдар

Қосымша файлдар
Әрекет
1. JATS XML

© Russian Academy of Sciences, 2023