Abstract
The review integrates and systematically describes data on the methods of synthesis, reactivity and biological activity of
3-nitro-2H-chromenes published over the last five years and data on 3-nitro-4H-chromenes and related 3-nitro-4H-pyrans published over the whole investigation period. Nucleophilic addition, including asymmetric synthesis, cycloaddition and redox reactions involving the C=C double bond and the nitro group of 3-nitro-2H-chromenes, are considered. The transformations of new and poorly investigated 3-nitro-4H-chromenes include reactions of 4-sulfanyl-substituted 3-nitro-4H-chromenes with nucleophiles, reactions of the nitroenamine moiety and removal of the alkylsulfanyl group using reductive processes. Reaction mechanisms and stereochemistry of the reaction products are discussed.
The bibliography includes 103 references.
Funders
Ministry of Education and Science of the Russian Federation
02.А03.21.0006
References
1.
rcr_88_1_27_bib1
Schweizer
1977
2.
Horton D.A., Bourne G.T., Smythe M.L.
Chemical Reviews ,
2003
3.
O' Connor C.J., Beckmann H.S., Spring D.R.
Chemical Society Reviews ,
2012
4.
Pratap R., Ram V.J.
Chemical Reviews ,
2014
5.
Costa M., Dias T.A., Brito A., Proença F.
European Journal of Medicinal Chemistry ,
2016
6.
ELOMRI A., SKALTSOUNIS A., MICHEL S., TILLEQUIN F., KOCH M., ROLLAND Y., PIERRE A., ATASSI G.
Chemical and Pharmaceutical Bulletin ,
2011
7.
rcr_88_1_27_bib7
8.
rcr_88_1_27_bib8
Wang
J. Farm. Sci. ,
2017
9.
Han K., Xu X., Chen G., Zeng Y., Zhu J., Du X., Zhang Z., Cao B., Liu Z., Mao X.
Journal of Hematology and Oncology ,
2014
10.
Fouqué A., Delalande O., Jean M., Castellano R., Josselin E., Malleter M., Shoji K.F., Hung M.D., Rampanarivo H., Collette Y., van de Weghe P., Legembre P.
Journal of Medicinal Chemistry ,
2015
11.
Ito M., Egashira S., Yoshida K., Mineno T., Kumagai K., Kojima H., Okabe T., Nagano T., Ui M., Matsuoka I.
Life Sciences ,
2017
12.
rcr_88_1_27_bib12
Baker
J. Biol. Chem. ,
2007
13.
Granados-Covarrubias E.H., Maldonado L.A.
Journal of Organic Chemistry ,
2009
14.
Cueva J.P., Chemel B.R., Juncosa J.I., Lill M.A., Watts V.J., Nichols D.E.
European Journal of Medicinal Chemistry ,
2012
15.
Li P., Luo L., Li X., Xie J.
Tetrahedron ,
2010
16.
rcr_88_1_27_bib16
Guo
2012
17.
Korotaev V.Y., Barkov A.Y., Sosnovskikh V.Y.
Tetrahedron ,
2013
18.
Carroll A., Bowden B., Coll J.
Australian Journal of Chemistry ,
1993
19.
rcr_88_1_27_bib19
Wang
Neural Regen. Res. ,
2010
20.
Buckner S.A., Milicic I., Daza A., Davis-Taber R., Scott V.E., Sullivan J.P., Brioni J.D.
European Journal of Pharmacology ,
2000
21.
Lal J.
Contraception ,
2010
22.
Evans C., Davis L.
Molecules ,
2017
23.
Korotaev V.Y., Sosnovskikh V.Y., Barkov A.Y.
Russian Chemical Reviews ,
2013
24.
rcr_88_1_27_bib24
Majumdar
ACSCatal ,
2015
25.
26.
rcr_88_1_27_bib26
Halimehjani
RSC Adv. ,
2014
27.
rcr_88_1_27_bib27
Halimehjani
RSC Adv. ,
2014
28.
Singh M.S., Chowdhury S., Koley S.
Tetrahedron ,
2016
29.
Döndas H., de Gracia Retamosa M., Sansano J.
Synthesis ,
2017
30.
Rao H.S., Geetha K.
Tetrahedron Letters ,
2009
31.
Zhang L., Dong J., Xu X., Liu Q.
Chemical Reviews ,
2016
32.
Zhang D., Ma Y., Liu Y., Liu Z.
Archiv der Pharmazie ,
2014
33.
rcr_88_1_27_bib33
34.
rcr_88_1_27_bib34
35.
Tan S., He F., Kong T., Wu J., Liu Z.
Bioorganic and Medicinal Chemistry ,
2017
36.
Schwendt G., Glasnov T.
Monatshefte fur Chemie ,
2016
37.
Barkov A.Y., Korotaev V.Y., Kotovich I.V., Zimnitskiy N.S., Kutyashev I.B., Sosnovskikh V.Y.
Chemistry of Heterocyclic Compounds ,
2016
38.
Korotaev V.Y., Kutyashev I.B., Barkov A.Y., Sosnovskikh V.Y.
Chemistry of Heterocyclic Compounds ,
2017
39.
rcr_88_1_27_bib39
Jalal
2013
40.
Climent M.J., Iborra S., Sabater M.J., Vidal J.D.
Applied Catalysis A: General ,
2014
41.
rcr_88_1_27_bib41
Liu
Synthesis ,
2016
42.
rcr_88_1_27_bib42
Yin
2013
43.
Li M., Zhao X., Yang W., Zhong F., Yuan L., Ren Q.
Tetrahedron Letters ,
2018
44.
Soengas R.G., Rodríguez-Solla H., Silva A.M., Llavona R., Paz F.A.
Journal of Organic Chemistry ,
2013
45.
Krishnammagari S.K., Lim K.T., Cho B.G., Tae Jeong Y.
Phosphorus, Sulfur and Silicon and the Related Elements ,
2018
46.
Parthiban A., Muthukumaran J., Moushumi Priya A., Jayachandran S., Krishna R., Surya Prakash Rao H.
Medicinal Chemistry Research ,
2013
47.
rcr_88_1_27_bib47
Kamalraja
Synthesis ,
2012
48.
Jadhav A.M., Krishnammagari S.K., Kim J.T., Jeong Y.T.
Tetrahedron ,
2017
49.
Gunasekaran P., Prasanna P., Perumal S., Almansour A.I.
Tetrahedron Letters ,
2013
50.
Wang J., Zhao Z., Li Z., Mao J., Zhang W., Guo C.
Chemistry of Heterocyclic Compounds ,
2018
51.
Kamalraja J., Perumal P.T.
Tetrahedron Letters ,
2014
52.
Perumal P., Poomathi N., Kamalraja J., Mayakrishnan S., Muralidharan D.
Synlett ,
2014
53.
Osyanin V.A., Lukashenko A.V., Osipov D.V., Klimochkin Y.N.
Chemistry of Heterocyclic Compounds ,
2015
54.
Wu N., Wahl B., Woodward S., Lewis W.
Chemistry - A European Journal ,
2014
55.
Li J., Du D.
Organic and Biomolecular Chemistry ,
2015
56.
Li J., Du D.
Organic and Biomolecular Chemistry ,
2015
57.
Kumar M., Chauhan P., Valkonen A., Rissanen K., Enders D.
Organic Letters ,
2017
58.
Yang W., He H., Gao Y., Du D.
Advanced Synthesis and Catalysis ,
2013
59.
Tan F., Lu L., Yang Q., Guo W., Bian Q., Chen J., Xiao W.
Chemistry - A European Journal ,
2014
60.
rcr_88_1_27_bib60
Fu
RSC Adv. ,
2014
61.
Mohapatra S., Bhakta S., Chakroborty S., Tripathy M., Nayak S.
Research on Chemical Intermediates ,
2014
62.
Ghosh M., Santra S., Mondal P., Kundu D., Hajra A.
Chemistry - An Asian Journal ,
2015
63.
Jiang W., Sun J., Liu R., Yan C.
Organic and Biomolecular Chemistry ,
2018
64.
Korotaev V.Y., Kutyashev I.B., Barkov A.Y., Sosnovskikh V.Y.
Tetrahedron ,
2017
65.
Korotaev V.Y., Barkov A.Y., Matochkina E.G., Kodess M.I., Sosnovskikh V.Y.
Tetrahedron ,
2014
66.
Korotaev V.Y., Kotovich I.V., Barkov A.Y., Kutyashev I.B., Kodess M.I., Sosnovskikh V.Y.
Tetrahedron ,
2016
67.
Korotaev V.Y., Kutyashev I.B., Barkov A.Y., Sosnovskikh V.Y.
Chemistry of Heterocyclic Compounds ,
2015
68.
Korotaev V.Y., Barkov A.Y., Kutyashev I.B., Kotovich I.V., Ezhikova M.A., Kodess M.I., Sosnovskikh V.Y.
Tetrahedron ,
2015
69.
Korotaev V.Y., Barkov A.Y., Ezhikova M.A., Kodess M.I., Sosnovskikh V.Y.
Chemistry of Heterocyclic Compounds ,
2015
70.
Korotaev V.Y., Kutyashev I.B., Barkov A.Y., Ezhikova M.A., Kodess M.I., Sosnovskikh V.Y.
Chemistry of Heterocyclic Compounds ,
2015
71.
rcr_88_1_27_bib71
Wang
Arkivoc
72.
Zhang L., Sun J., Yan C.
Chinese Journal of Chemistry ,
2013
73.
Fang J., Yan C.
Journal of Heterocyclic Chemistry ,
2015
74.
Sun Q., Sun J., Jiang W., Yan C.
Tetrahedron ,
2018
75.
rcr_88_1_27_bib75
Sharma
J. Braz. Chem. Soc ,
2017
76.
Quan X., Ren Z., Wang Y., Guan Z.
Organic Letters ,
2014
77.
Chen Z., Zheng Y., Ma J.
Angewandte Chemie - International Edition ,
2017
78.
79.
rcr_88_1_27_bib79
Jiang
RSC Adv. ,
2017
80.
Naga Siva Rao J., Raghunathan R.
Tetrahedron Letters ,
2013
81.
rcr_88_1_27_bib81
Rao
Tetrahedron Lett.
82.
Nayak S., K. Mishra S., Bhakta S., Panda P., Baral N., Mohapatra S., S. Purohit C., Satha P.
Letters in Organic Chemistry ,
2015
83.
Wu S., Zhu G., Wei S., Chen H., Qu J., Wang B.
Organic and Biomolecular Chemistry ,
2018
84.
Korotaev V.Y., Kutyashev I.B., Barkov A.Y., Sosnovskikh V.Y.
Chemistry of Heterocyclic Compounds ,
2017
85.
Barkov A.Y., Zimnitskiy N.S., Kutyashev I.B., Korotaev V.Y., Sosnovskikh V.Y.
Tetrahedron Letters ,
2017
86.
Li S., Xu H., Cui S., Wu F., Zhang Y., Su M., Gong Y., Qiu S., Jiao Q., Qin C., Shan J., Zhang M., Wang J., Yin Q., Xu M., et. al.
Journal of Medicinal Chemistry ,
2016
87.
Baryshnikova M.A., Volkonskii A.Y., Gusev D.V., Labodneva N.O., Sigan A.L., Yakunina N.G., Chkanikov N.D.
Russian Chemical Bulletin ,
2014
88.
Wang C., Qing X., Wang T., Dai C., Su Z.
Synthesis ,
2017
89.
Ahmed N., Pathe G.
Synthesis ,
2015
90.
Zhao D., Zhu Y., Guo S., Chen W., Zhang G., Yu Y.
Tetrahedron ,
2017
91.
Zhao D., Guo S., Guo X., Zhang G., Yu Y.
Tetrahedron ,
2016
92.
rcr_88_1_27_bib92
Ibrahim
2014
93.
Rao V.R., Suresh G., Babu K.S., Raju S.S., Vishnu vardhan M.V., Ramakrishna S., Rao J.M.
Tetrahedron ,
2011
94.
Parthiban A., Kumaravel M., Muthukumaran J., Rukkumani R., Krishna R., Rao H.S.
Medicinal Chemistry Research ,
2016
95.
Parthiban A., Muthukumaran J., Manhas A., Srivastava K., Krishna R., Rao H.S.
Bioorganic and Medicinal Chemistry Letters ,
2015
96.
Surya Prakash Rao H., Geetha K., Kamalraj M.
RSC Advances ,
2011
97.
Rao H.S., Tangeti V.S., Adigopula L.N.
Research on Chemical Intermediates ,
2016
98.
RAO H.S., TANGETI V.S.
Journal of Chemical Sciences ,
2013
99.
Rao H.S., Adigopula L.N., Ramadas K.
ACS Combinatorial Science ,
2017
100.
101.
rcr_88_1_27_bib101
Rao
2014
102.
Rahmani-Nezhad S., Safavi M., Pordeli M., Ardestani S.K., Khosravani L., Pourshojaei Y., Mahdavi M., Emami S., Foroumadi A., Shafiee A.
European Journal of Medicinal Chemistry ,
2014
103.
Galano J.J., Alías M., Pérez R., Velázquez-Campoy A., Hoffman P.S., Sancho J.
Journal of Medicinal Chemistry ,
2013