Abstract
The Friedel–Crafts-type reaction of 5-allyl-2,3,5-trichlorocyclopent-2-enones with mono-, di- and trimethoxybenzenes affords the arene ketovinylation products with the cleavage of C3–Cl bond in the starting trichlorocyclopentenones. The cytotoxocity of the products toward normal HEK293 cell lines and three cancer cell lines, SH-SY5Y, A549 and MCF-7, was evaluated.
References
1.
Olah G.A.
Accounts of Chemical Research,
1971
2.
3.
Gore P.H.
Chemical Reviews,
1955
4.
Feofanov M.N., Lozhkin B.A., Anokhin M.V., Averin A.D., Beletskaya I.P.
Mendeleev Communications,
2018
5.
Sartori G., Maggi R.
Chemical Reviews,
2006
6.
Sartori G., Maggi R.
Chemical Reviews,
2011
7.
Akhmetvaleev R.R., Akbutina F.A., Ivanova N.A., Miftakhov M.S.
Russian Chemical Bulletin,
2001
8.
10.1016/j.mencom.2019.03.019_bib0035
Ismailov
J. Org. Chem. USSR (Engl. Transl.),
1989
9.
10.1016/j.mencom.2019.03.019_bib0040
Ivanova
Russ. J. Org. Chem.,
1999
10.
Gimalova F.A., Gavrilov O.A., Torosyan S.A., Miftakhov M.S.
Russian Journal of Organic Chemistry,
2006
11.
Hussain M., Hung N.T., Khera R.A., Villinger A., Langer P.
Tetrahedron Letters,
2011
12.
Zinad D.S., Hussain M., Villinger A., Langer P.
European Journal of Organic Chemistry,
2011
13.
Khera R.A., Hussain M., Hung N.T., Eleya N., Feist H., Villinger A., Langer P.
Helvetica Chimica Acta,
2012
14.
Gimalova F.A., Egorov V.A., Selezneva N.K., Miftakhov M.S.
Russian Journal of Organic Chemistry,
2006
15.
Ivanova N.A., Shainurova A.M., Furlei I.I., Miftakhov M.S.
Russian Chemical Bulletin,
1996
16.
Bozhenkov G.V., Leckovskaya G.G., Larina L.I., Ushakov P.E., Dolgushin G.V., Mirskova A.N.
Russian Journal of Organic Chemistry,
2004
17.
Ivanovsky S.A., Dorogov M.V., Kravchenko D.V., Ivachtchenko A.V.
Synthetic Communications,
2007
18.
Xie J., Comeau A.B., Seto C.T.
Organic Letters,
2003
19.
Kim H.Y., Oh K.
Organic Letters,
2014
20.
Oh K., Kim H., Cardelli F., Bwititi T., Martynow A.M.
Journal of Organic Chemistry,
2008
21.
Kim H.Y., Song E., Oh K.
Organic Letters,
2016
22.
Piska K., Gunia-Krzyżak A., Koczurkiewicz P., Wójcik-Pszczoła K., Pękala E.
European Journal of Medicinal Chemistry,
2018
23.
Hori H.
Bioorganic and Medicinal Chemistry,
2002
24.
Li X., Ferreira D., Jacob M.R., Zhang Q., Khan S.I., ElSohly H.N., Nagle D.G., Smillie T.J., Khan I.A., Walker L.A., Clark A.M.
Journal of the American Chemical Society,
2004