Catalytic Rearrangement of Four Substituted Tetrahydropyridine

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Аннотация

A new compound, 5-acetyl-2-amino-4-(2-chloro-5-nitrophenyl)-6-oxo-1-phenyl-1,4,5,6-tetrahydropyridine-3-carbonitrile, was synthesized by the reaction of 2-chloro-5-nitrobenzylidenemalononitrile with malononitrile and aniline. Subsequently, it was subjected to catalytic rearrangement in the presence of ethylenediamine and a second new compound, 4-(2-chloro-5-nitrophenyl)-6-oxo-2-(phenylamino)-1,4,5,6-tetrahydropyridine-3-carbonitrile, was obtained. The structure of the products was determined using NMR spectroscopy and X-ray diffraction analysis. A probable mechanism of the rearrangement reaction was proposed.

Авторлар туралы

F. Naghiyev

Baku State University

ORCID iD: 0009-0003-9325-1756
Baku, Azerbaijan

V. Khrustal'ev

Peoples' Friendship University of Russia (RUDN University); N.D. Zelinsky Institute of Organic Chemistry RAS

ORCID iD: 0000-0001-8806-2975
Moscow, Russia; Moscow, Russia

M. Komarovskikh

Peoples' Friendship University of Russia (RUDN University)

ORCID iD: 0009-0004-6733-2322
Moscow, Russia

M. Tachaev

Peoples' Friendship University of Russia (RUDN University)

ORCID iD: 0000-0003-3606-0868
Moscow, Russia

I. Mamedov

Baku State University

Email: bsu.mmrtab@gmail.com
ORCID iD: 0000-0002-5757-9899
Baku, Azerbaijan

Әдебиет тізімі

  1. Taylor A.P., Robinson R.P., Fobian Y.M., Blakemore D.C., Jones L.H., Fadeyi O., Org. Biomol. Chem., 2016, 14, 6611–6687. doi: 10.1039/C60B00936K
  2. Cabrele C., Reiser O., J. Org. Chem., 2016, 81, 10109–10125. doi: 10.1021/acs.joc.6b02034
  3. Elinson M.N., Ryzhkov F.V., Vereshchagin A.N., Zaimovskaya T.A., Korolev V.A., Egorov M.P., Mendeleev Commun., 2016, 26, 399–401. doi: 10.1016/j.mencom.2016.09.011
  4. Mamedov I.G., Naghiev F.N., Maharramov A.M., Uwangue O., Farewell A., Sunneringen P., Erdelyi M., Mendeleev Commun., 2020, 30, 498–499. doi: 10.1016/j.mencom.2020.07.031
  5. Haihua X., Pingliang L., Dongcai G., Jinhui H., Yuchao C., Wei H., Med. Chem. Res., 2014, 23, 1941–1949. doi: 10.1007/s00044-013-0790-2
  6. Chapyshev S.V., Kuzina S.I., Mikhailov A.I., Mendeleev Commun., 2007, 17, 207–208. doi: 10.1016/j.mencom.2007.06.006
  7. Ashraf H.A., Dalal A.A., Jochen L., Heather N.T., Bernard D.G., Gary A.P., Mohammed A.O.A., Eur. J. Med. Chem., 2010, 45, 90–97. doi: 10.1016/j.ejmech.2009.09.029
  8. Amal A.M.E., Nahla A.H.F., Gamal A.H.S., Bioorg. Med. Chem., 2009, 17, 5059–5070. doi: 10.1016/j.bmc.2009.05.073
  9. Rupert K.C., Henry J.R., Dodd J.H., Wadsworth S.A., Cavender D.E., Olini G.C., Fahmy B., Siekierka J.J., Bioorg. Med. Chem. Lett., 2003, 13, 347–350. doi: 10.1016/S0960-894X(02)01020-X
  10. Esatbeyoglu T., Wagner A., Schini-Kerth V.B., Rimbach G., Mol. Nutr. Food Res., 2015, 59, 36–47. doi: 10.1002/mnfr.201400484
  11. Kesting J.R., Tolderlund I.L., Pedersen A.F., Witt M., Jaroszewski J.W., Staerk D., J. Nat. Prod., 2009, 72, 312–315. doi: 10.1021/np800743w
  12. Khumalo M., Maddila S.N., Maddila S., Jonnalagadda S.B., J. Chem. Sci., 2020, 132, 1–6. doi: 10.1007/s12039-019-1725-3
  13. Aiello D., Jonas H., Carbone A., Carbone D., Pecoraro C., Tesoriere L., Köhler J., Wunsch B., Diana P., Molecules, 2022, 27, 7423. doi: 10.3390/molecules27217423

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