2-Ylidene-1,3-thiazolidines and their nonhydrogenated analogs: methods of synthesis and chemical properties
- PDF / 759,950 Bytes
- 16 Pages / 594 x 792 pts Page_size
- 35 Downloads / 182 Views
2-Ylidene-1,3-thiazolidines and their nonhydrogenated analogs: methods of synthesis and chemical properties Mariia B. Litvinchuk1*, Anton V. Bentya1, Nataliia Yu. Slyvka2, Mikhailo V. Vovk1 1
Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02094, Ukraine; e-mail: [email protected] 2 Lesya Ukrainka Eastern European National University, 13 Voli Ave., Lutsk 43025, Ukraine; e-mail: [email protected] Submitted April 7, 2020 Accepted after revision May 29, 2020
Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(9), 1130–1145
R1
R2
S
R1 +
C
S H2C
Cl
N
R2 NH
S R1
R
R2 O
N
R2
R1
O
+
+ R2 NH2
1
R1
SH 1
OEt
R1
R2
2
S
O
2'
5
or
NH
S
3
R2 NH
R1
MeS H2N
SMe +
SH
4
R1, R2 = Alk, CN, CO2Et E/Z-isomerization Electrophilic functionalization reactions Cyclocondensation reactions
The review summarizes and systematizes the literature data on the methods of synthesis and chemical properties of 2-ylidene-1,3thiazolidines and 2-ylidene-2,3-dihydro-1,3-thiazoles. Two general approaches to their preparation have been identified: the construction of the 2-ylidene-1,3-thiazolidine ring from acyclic precursors in one synthetic process and the introduction of the 2-ylidene fragment into the 1,3-thiazolidine ring. The main chemical transformations of 2-ylidene-1,3-thiazolidines and 2-ylidene-2,3-dihydro-1,3-thiazoles, which include the reactions of selective functionalization and heterocyclization at the ylidene fragment and thiazolidine backbone, are considered. The bibliography of the review consists of 97 references published from 2000 to 2020.
Keywords: 2-ylidene-1,3-thiazolidines, 2-ylidene-2,3-dihydro-1,3-thiazoles, cyclocondensation, electrophilic cyclization, functionalization. 2-Ylidene-1,3-thiazolidines and their nonhydrogenated analogs 2-ylidene-2,3-dihydro-1,3-thiazoles have attracted close attention of researchers in the last two decades as promising heterocyclic systems that significantly complement the synthetic and biological potential of the wellstudied 4-thiazolidinones occupying one of the key positions in modern medicinal chemistry.1,2 Derivatives of 2-ylidene-1,3-thiazolidines are used in heterocyclic chemistry as valuable synthetic blocks.3–7 They are characterized by a pronounced spectrum of bactericidal,8 antitumor,9 anti-inflammatory10 properties, and also act as noncompetitive inhibitors of metalloproteinase aggrecanase11 and phospholipase A2.12 In turn, 2,3-dihydro-1,3-thi0009-3122/20/56(9)-1130©2020 Springer Science+Business Media, LLC
azole derivatives exhibit antiparasitic activity against Trypanosoma bruceі,13 and also serve as ligands for cannabinoid CB214 receptors and inhibitors of kinases GSK3 β and JNK3.15 No less significant is the recently discovered property of a derivative of 2-(1,1-dicyanomethylene)rhodanine, a representative of this type of compounds, to act as an effective acceptor in the design of dye-sensitized solar cells.16-21 In light of the above, the creation of new and improveme
Data Loading...
