Current approaches to the synthesis of 4-arylcoumarins (neoflavones) are reviewed. This is an important group of O-containing natural flavonoids that are widely used not only to prepare natural and synthetic neoflavone analogs but also to design compound libraries based on 4-arylcoumarins for biological activity studies. The use of new transition-metal catalysts and unconventional activation methods for cyclization of the coumarin system, arylation of activated coumarins, and direct arylation of unactivated coumarins are discussed.
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R. D. H. Murray, Nat. Prod. Rep., 12, 477 (1995).
A. Estevez-Braun and A. G. Gonzalez, Nat. Prod. Rep., 14, 465 (1997).
V. M. Malikov and A. I. Saidkhodzhaev, Chem. Nat. Compd., 34, 250 (1998).
A. Ormancey-Potier, A. Buzas, and E. Lederer, Bull. Soc. Chim. Fr., 577 (1951).
P. M. Dewick, “Isoflavonoids,” in: The Flavonoids: Advances in Research Since 1986, Chapman and Hall, London, 1986, p. 117.
D. M. X. Donnelly and G. Boland, “Neoflavonoids,” in: The Flavonoids: Advances in Research Since 1994, Chapman and Hall, London, 1994, p. 239.
G. D. Monachep, B. Borr, A. S. Neto, and R. A. De Lima, Phytochemistry, 22, 1657 (1983).
D. M. X. Donnelly, J.-P. Finet, P. J. Guiry, and R. M. Hutchinson, J. Chem. Soc., Perkin Trans., 2851 (1990).
M. Costa, T. Dias, A. Brito, and F. Proenca, Eur. J. Med. Chem., 123, 487 (2016).
M. V. Kulkarni, G. M. Kulkarni, Ch.-H. Lin, and Ch.-M. Sun, Curr. Med. Chem., 13 (23), 2795 (2006).
M. del R. Garcia, F. Calzada, and R. Mata, Rev. Latinoam. Quim., 21 (3–4), 122 (1990).
T. Ishikawa, Heterocycles, 53 (2), 453 (2000).
M. M. Garazd, Ya. L. Garazd, and V. P. Khilya, Chem. Nat. Compd., 39, 54 (2003).
D. M. X. Donnelly, “Neoflavonoids,” in: The Flavonoids, J. B. Harborne and T. J. Mabry, Chapman & Hall, London, 1975, 801 pp.
R. D. H. Murray, J. Mendez, and S. A. Brown, The Natural Coumarins – Occurrence, Chemistry and Biochemistry, John Wiley & Sons Ltd., New York, 1982.
L. Wang, T. Ma, and G. Liu, “Recent Progress in Calophyllum Coumarins as Potent Anti-HIV Agents,” in: Medicinal Chemistry of Bioactive Natural Products, X.-T. Liang and W.-Sh. Fang, John Wiley & Sons, Inc., Hoboken, N. J., 2006, pp. 325–355.
M. M. Garazd, Ya. L. Garazd, and V. P. Khilya, Chem. Nat. Compd., 41, 245 (2005).
Priyanka, R. K. Sharma, and D. Katiyar, Synthesis, 48 (15), 2303 (2016).
A. Yu. Fedorov, A. V. Nyuchev, and I. P. Beletskaya, Chem. Heterocycl. Compd., 48 (1), 166 (2012).
M. A. Salem, M. H. Helal, M. A. Gouda, Y. A. Ammar, M. S. A. El-Gaby, and S. Y. Abbas, Synth. Commun., 48 (13), 1534 (2018).
A. Thakur, R. Singla, and V. Jaitak, Eur. J. Med. Chem., 101, 476 (2015).
S. Singal, S. L. Jain, and B. Sain, Heterocycles, 75 (5), 1205 (2008).
M. Sowmiya, A. Sharma, S. Parsodkar, and B. G. Mishra, Appl. Cat., A, 333 (2), 272 (2007).
S. Kumar, A. Saini, and J. Sandhu, ARKIVOC, 15, 18 (2000).
M. A. Naik, B. G. Mishra, and A. Dubey, React. Kinet. Catal. Lett., 91 (1), 169 (2007).
M. Dabiri, P. Salehi, M. A. Zolfigol, and M. Baghbanzadeh, Heterocycles, 71 (3), 677 (2007).
B. S. Kumar, P. S. Kumar, N. Srinivasulu, B. Rajitha, Y. Th. Reddy, P. N. Reddy, and R. H. Udupi, Chem. Heterocycl. Compd., 42 (2), 172 (2006).
B. S. Kumar, Y. T. Reddy, P. N. Reddy, P. S. Kumar, and B. Rajitha, J. Heterocycl. Chem., 43 (2), 477 (2006).
B.-L. Zhang, F.-D. Wang, and J.-M. Yue, Synlett, 4, 567 (2006).
I. A. Rosa, L. Almeida, K. F. Alves, M. J. Marques, A. M. Fregnan, C. A. Silva, J. O. S. Giacoppo, T. C. Ramalho, D. T. Carvalho, and M. H. Santos, Med. Chem. Res., 26, 131 (2017).
Ch.-F. Liu, Q.-K. Shen, J.-J. Li, Yu-Sh. Tian, and Zh. Quan, J. Enzyme Inhib. Med. Chem., 32 (1), 1111 (2017).
M. S. Manhas, S. N. Ganguly, S. Mukherjee, A. K. Jain, and A. K. Bose, Tetrahedron Lett., 47 (14), 2423 (2006).
S. Teizo and T. Koichi, Chem. Lett., 2, 110 (2001).
S. Patil, R. Bhat, V. Raje, and S. Samant, Synth. Commun., 36 (4), 525 (2006).
A. M. Varughese, B. P. Ramakrishna, and S. D. Shriniwas, Tetrahedron Lett., 46 (40), 6957 (2005).
G. V. M. Sharma, J. J. Reddy, P. S. Lakshmi, and P. R. Krishna, Tetrahedron Lett., 46 (36), 6119 (2005).
S. R. Pankajkumar, S. U. Devendrapratap, and S. D. Shriniwas, Synlett, 11, 1909 (2004).
E. Sekino, T. Kumamoto, T. Tanaka, T. Ikeda, and T. Ishikawa, J. Org. Chem., 69 (8), 2760 (2004).
A. C. Khandekar and B. M. Khadikar, Synlett, 1, 152 (2002).
J.-M. Lee, T.-H. Tseng, and Y.-J. Lee, Synthesis, 15, 2247 (2001).
M. Opanasenko, M. Shamzhy, and J. Cejka, ChemCatChem, 5, 1024 (2013).
M. V. Paradkar, M. S. Kulkarni, and S. A. Kulkarni, Org. Prep. Proced. Int., 28 (3), 348 (1996).
A. K. Ganguly, B. S. Joshi, V. N. Kamat, and A. H. Manmade, Tetrahedron, 12, 4777 (1967).
N. L. Polyanskaya, S. P. Starkov, and M. N. Volkotrub, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 35 (1), 26 (1992).
P. Satyanarayana, Curr. Sci., 49 (15), 592 (1980).
L. L. Woods and V. Hollands, Tex. J. Sci., 21 (1), 91 (1969).
Y. Yamamoto, Chem. Soc. Rev., 43, 1575 (2014).
J. Oyamada and T. Kitamura, Tetrahedron, 62 (29), 6918 (2006).
J. Oyamada and T. Kitamura, Chem. Lett., 34 (10), 1430 (2005).
J. Oyamada and T. Kitamura, Tetrahedron Lett., 46, 3823 (2005).
M. Kotani, K. Yamamoto, and J. Oyamada, Synthesis, 9, 1466 (2004).
T. Kitamura, K. Yamamoto, and M. Kotani, Bull. Chem. Soc. Jpn., 76 (10), 1889 (2003).
B. M. Trost, F. D. Toste, and K. Greenman, J. Am. Chem. Soc., 125 (15), 4518 (2003).
J. Oyamada, Ch. Jia, Y. Fujiwara, and T. Kitamura, Chem. Lett., 3, 380 (2002).
T. Kitamura, J. Ojamada, and T. Tsubota, Nat. Prod., 2 (4), 845 (2007).
B. M. Trost and F. D. Toste, J. Am. Chem. Soc., 118 (26), 6305 (1996).
S. J. Pastine, S. W. Youn, and D. Sames, Tetrahedron, 59 (45), 8859 (2003).
K. M. Shamsuddin and M. J. A. Siddiqui, J. Chem. Res., Synop., 7, 392 (1998).
P. Yu. Savechenkov, A. P. Rudenko, A. V. Vasil’ev, and G. K. Fukin, Russ. J. Org. Chem., 41 (9), 1316 (2005).
J. Sun, W.-X. Ding, X.-P. Hong, K.-Yu. Zhang, and Y. Zou, Chem. Nat. Compd., 48, 16 (2012).
J. Sun, W.-X. Ding, K.-Yu. Zhang, and Yo Zou, Chin. Chem. Lett., 22, 667 (2011).
A. M. Escobar, D. M. Ruiz, J. C. Autino, and G. P. Romanelli, Res. Chem. Intermed., 41 (12), 10109 (2015).
D. K. Rayabarapu, T. Sambaiah, and Ch.-H. Cheng, Angew. Chem., Int. Ed., 40 (7), 1286 (2001).
M. Y. Yoon, J. H. Kim, D. S. Choi, et al., Adv. Synth. Catal., 349 (10), 1725 (2007).
Ch. E. Song, D. Jun, S. Y. Choung, et al., Angew. Chem., Int. Ed., 43 (45), 6183 (2004).
B. Wang, Na Li, T. Liu, J. Sun, and X. Wang, RSC Adv., 7, 34448 (2017).
R. Li, S. R. Wang, and W. Lu, Org. Lett., 9 (11), 2219 (2007).
C. Jia, D. Piao, T. Kitamura, and Y. Fujiwara, J. Org. Chem., 65 (22), 7516 (2000).
C. Jia, W. Lu, and J. Oyamada, J. Am. Chem. Soc., 122 (30), 7252 (2000).
K. Li, Y. Zeng, B. Neuenswander, and J. A. Tunge, J. Org. Chem., 70 (16), 6515 (2005).
Z. Shi and C. He, J. Org. Chem., 69, 3669 (2004).
Y. Yamamoto and N. Kirai, Org. Lett., 10 (24), 5513 (2008).
T. Sasaki, K. Moriyama, and H. Togo, Beilstein J. Org. Chem., 14, 345 (2018).
X. Mi, Ch. Wang, M. Huang, Yu. Wu, and Ya Wu, J. Org. Chem., 80 (1), 148 (2015).
K. Yan, D. Yang, W. Wei, F. Wang, Yu. Shuai, Q. Li, and H. Wang, J. Org. Chem., 80 (3), 1550 (2015).
C. Pan, R. Chen, W. Shao, and J. T. Yu, Org. Biomol. Chem., 14, 9033 (2006).
S. Feng, X. Xie, and W. Zhang, Org. Lett., 18, 3846 (2016).
T. Liu, Q. Ding, Q. Zong, and G. Qiu, Org. Chem. Front., 2, 670 (2015).
G. Qiu, T. Liu, and Q. Ding, Org. Chem. Front., 3, 510 (2016).
T. Liu, Q. Din, G. Qiu, and J. Wu, Tetrahedron, 72, 279 (2017).
K. Kawaai, T. Yamaguchi, E. Yamaguchi, S. Endo, N. Tada, A. Ikari, and A. Itoh, J. Org. Chem., 83, 1988 (2018).
Y. Li, Y. Lu, G. Qiu, and Q. Ding, Org Lett., 16, 4240 (2014).
W. Fu, M. Zhu, G. Zou, Ch. Xu, Zh. Wang, and B. Ji, J. Org. Chem., 80 (9), 4766 (2015).
M. Zhu, W. Fu, Z. Wang, C. Xu, and B. Ji, Org. Biomol. Chem., 15, 9057 (2017).
Y. F. Zeng, D. H. Tan, and Y. Chen, Org. Chem. Front., 2, 1511 (2015).
X. Mi, C. Wang, M. Huang, J. Zhang, Y. Wu, and Y. Wu, Org. Lett., 16, 3356 (2014).
D. Liu, J. Q. Chen, X. Z. Wang, and P. F. Xu, Adv. Synth. Catal., 359, 2773 (2017).
A. C. Mantovani, T. A. C. Goulart, D. F. Back, P. H. Menezes, and G. J. Zeni, J. Org. Chem., 79, 10526 (2014).
W. Wei, J. Wen, and D. Yang, Chem. Commun., 51, 768 (2015).
W. C. Gao, T. Liu, and B. Zhang, J. Org. Chem., 81, 11297 (2016).
W. Wu, Y. An, J. Li, S. Yang, Z. Zhu, and H. Jiang, Org. Chem. Front., 4, 1751 (2017).
D. Zheng, J. Yu, and J. Wu, Angew. Chem., Int. Ed., 55, 11925 (2016).
S. Ni, J. Cao, H. Mei, J. Han, S. Li, and Y. Pan, Green Chem., 18, 3935 (2016).
Y. Yu, S. Zhuang, P. Liu, and P. Sun, J. Org. Chem., 81, 11489 (2016).
W. Zhang, Ch. Yang, Yu-L. Pan, X. Li, and J.-P. Cheng, Org. Biomol. Chem., 16, 5788 (2018).
N. Li, B. Wang, J.-Y. Sun, X.-J. Wang, and J. Sun, Chem. Nat. Compd., 53, 860 (2017).
J. Singh, J. Kaur, S. Nayyar, and G. L. Kad, J. Chem. Res., Synop., 5, 280 (1998).
E. Rizzi, S. Dallavalle, L. Merlini, G. Pratesi, and F. Zunino, Synth. Commun., 36 (8), 1117 (2006).
H. Krawczyk, L. Albrecht, J. Wojciechowski, and W. M. Wolf, Tetrahedron, 63, 12583 (2007).
Sh. Aoki, J. Oyamada, and T. Kitamura, Bull. Chem. Soc. Jpn., 78 (3), 468 (2005).
G. Battistuzzi, S. Cacchi, I. De Salve, G. Fabrizi, and L.M. Parisi, Adv. Synth. Catal., 347 (2+3), 308 (2005).
D. Sharma, C. B. Reddy, A. K. Shil, R. P. Saroach, and P. Das, Mol. Diversity, 17 (4), 651 (2013).
S. X. Cai, H. Zhang, W. E. Kemmitzer, S. Jiang, J. A. Drewe, and R. Storer, Patent WO 2002092076 USA, “Substituted coumarins and quinolinones as caspase activators ,” Shire Biochem., Inc., Nov. 21, 2002.
T. V. Krishnamoorthy, K. Rajagopalan, and K. K. Balasubramanian, Tetrahedron Lett., 26 (14), 1747 (1985).
D. A. Barancelli, Jr., A. G. Salles, J. G. Taylor, and C. R. D. Correia, Org. Lett., 14 (23), 6036 (2012).
Q. Yang, Z. Jia, L. Li, L. Zhang, and S. Luo, Org. Chem. Front., 5, 237 (2017).
K. Li and J. A. Tunge, J. Comb. Chem., 10 (2), 170 (2008).
A. K. Das Gupta, K. R. Das, and A. Das Gupta, Indian J. Chem., 10 (1), 32 (1972).
A. K. Das Gupta and M. S. Paul, J. Indian Chem. Soc., 47 (10), 1017 (1970).
Ng. Buu-Hoi, B. Ekert, and R. Royer, J. Org. Chem., 19 (9), 1548 (1954).
K. Sato and T. Amakasu, J. Org. Chem., 33 (6), 2446 (1968).
W. H. Perkin, J. Chem. Soc., 21, 53 (1868).
Y. Kawase, S. Yamaguchi, K. Aoyama, and M. Matsuda, Bull. Chem. Soc. Jpn., 51 (6), 1907 (1978).
S. P. Kamat, A. M. D’Souza, S. K. Paknikar, and Ph. S. Beauchamp, J. Chem. Res., Synop., 5, 242 (2002).
Sh. Indra and R. Suprabhat, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 27 (4), 374 (1988).
S. Kirkiacharian, A. Bigou, and R. Bakhchinian, Patent FR 2,849,653 France, “Preparation of coumarins having affinity estrogen receptors for treating neoplasm, in particular breast neoplasm,” B. F. B. Etudes Et Recherches Experimentales, Fr. - No. 2849653 A1, Sept. 7, 2004.
V. Narayanan and M. Natarajan, Indian J. Heterocycl. Chem., 2 (2), 69 (1992).
P. P. Rao and G. Srimannarayana, Synthesis, 11, 887 (1981).
V. K. Ahluwalia and C. H. Khanduri, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 27 (7), 599 (1989).
V. O. Patil, Sh. L. Kelkar, and M. S. Wadia, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 26 (7), 674 (1987).
B. P. Bandgar, L. S. Uppalla, and V. S. Sadavarte, J. Chem. Res., Synop., 40 (2002).
B. Sreenivasulu and P. N. Sarma, Synth. Commun., 26, 3373 (1996).
S. H. Mashraqui, D. Vashi, and H. D. Mistry, Synth. Commun., 34, 3129 (2004).
J. Crecente-Campo, M. P. Vazquez-Tato, and J. A. Seijas, Eur. J. Org. Chem., 4130 (2010).
O. Dischendorf and W. Limontschew, Monatsh. Chem., 80, 58 (1949).
W. Limontschew and O. Dischendorf, Monatsh. Chem., 81, 737 (1950).
R. D. Desai and C. K. Mavani, Proc. Indian Acad. Sci. A, 25, 353 (1947).
M. S. Raju and N. V. Subba Rao, Proc. Indian Acad. Sci. Sect. A., 79 (5), 223 (1974).
In-T. Hwang, S.-Ah Lee, J.-S. Hwang, and K.-In. Lee, Molecules, 16, 6313 (2011).
V. K. Ahluwalia, D. Singh, and R. P. Singh, Monatsh. Chem., 116 (6–7), 869 (1985).
R. Fortin, Y. Girard, E. Grimm, J. Hutchinson, and J. Scheigetz, Patent CA 2,125,824 Canada, “Heteroaryl coumaring as inhibitors of leukotriene biosynthesis,” Merck Frosst Canada Inc., Canada, No. 94-2125824 A1, Jun. 14,1994.
V. K. Ahluwalia, R. Gupta, and M. Grover, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 27 (12), 1138 (1988).
N. Britto, V. G. Gore, R. S. Mali, and A. C. Ranade, Synth. Commun., 19 (11–12), 1899 (1989).
B. D. Gallagher, B. R. Taft, and B. H. Lipshutz, Org. Lett., 11 (23), 5374 (2009).
F. Ulgheri, M. Marchetti, and O. Piccolo, J. Org. Chem., 72 (16), 6056 (2007).
H. Cao and W.-J. Xiao, Can. J. Chem., 83 (6–7), 826 (2005).
O. Piccolo, F. Ulgheri, and M. Marchetti, Patent WO 2005005356 Italy, “Enantioselective synthesis of enantiomerically enriched compounds,” Consiglio Nazionale Delle Ricerche, Italy, No. 2005005356 A2, Jan. 20, 2005.
K. H. Park, I. G. Jung, and Y. K. Chung, Synlett, 14, 2541 (2004).
D. V. Kadnikov and R. C. Larock, J. Org. Chem., 68 (24), 9423 (2003).
D. V. Kadnikov and R. C. Larock, Org. Lett., 2 (23), 3643 (2000).
H. Israr, S. Kaousar, N. Rasool, G. Ahmad, M. N. M. Aziz, M. N. Akhtar, and N. B. Alitheen, Preprints, 2017050115 (2017) (doi: 10.20944/preprints 201705.0115.v1).
M. A. Selepe and F. R. V. Heerden, Molecules, 18, 4739 (2013).
G. M. Boland, D. M. X. Donnelly, J.-P. Finet, and M. D. Rea, J. Chem. Soc., Perkin Trans. 1, No. 21, 2591 (1996).
L. Chen, T.-Sh. Hu, and Z.-Y. Yao, J. Org. Chem., 36, 6175 (2008).
D. M. X. Donnelly, J.-P. Finet, P. J. Guiry, and M. D. Rea, Synth. Commun., 29 (15), 2719 (1999).
L. Zhang, T. Meng, R. Fan, and J. Wu, J. Org. Chem., 72 (19), 7279 (2007).
Ch. Bally, Ch. Bal, and P. Barbier, J. Med. Chem., 46 (25), 5437 (2003).
L. Lunazzi, M. Mancinelli, A. Mazzanti, and M. Pierini, J. Org. Chem., 75 (17), 5927 (2010).
P. Yu. Wong, W. K. Chow, and K. H. Chung, Chem. Commun., 7 (29), 8328 (2011).
M. L. Yao and M.-Z. Deng, Heteroat. Chem., 11 (6), 380 (2000).
J. Wu, L. Wang, R. Fathi, and Zh. Yang, Tetrahedron Lett., 43 (24), 4395 (2002).
Y. Luo and J. Wu, Tetrahedron Lett., 50 (18), 2103 (2009).
P. Shah, M. D. Santana, et al., Tetrahedron, 69 (5), 1446 (2013).
Zh.-Yu Tang and Q.-Sh. Hu, Adv. Synth. Catal., 346 (13–15), 1635 (2004).
J. Wu, L. Zhang, and K. Gao, Eur. J. Org. Chem., 23, 5260 (2006).
J. Wu, L. Zhang, and Y. Luo, Tetrahedron Lett., 47 (38), 6747 (2006).
Ch.-H. Xing, Adv. Synth. Catal., 353 (11–12), 2051 (2011).
J. Kuroda, K. Inamoto, K. Hiroya, and T. Doi, Eur. J. Org. Chem., 14, 2251 (2009).
J. Wu, L. Zhang, and H.-G. Xia, Tetrahedron Lett., 47 (10), 1525 (2006).
A. N. Selikhov, Y. B. Malysheva, A. V. Nyuchev, N. S. Sitnikov, E. A. Sharonova, A. S. Shavyrin, S. Combes, and A. Yu. Fedorov, Russ. Chem. Bull., 60 (10), 2003 (2011).
M. I. Naumov, A. V. Nuchev, N. S. Sitniokov, Yu. B. Malysheva, A. S. Shavyrin, I. P. Beletskaya, A. E. Gavryushin, S. Combes, and A. Yu. Fedorov, Synthesis, 10, 1673 (2009).
I. P. Beletskaya, O. G. Ganina, and A. V. Tsvetkov, Synlett, 15, 2797 (2004).
O. G. Ganina, E. Daras, and V. Bourgarel-Rey, Bioorg. Med. Chem., 16 (19), 8806 (2008).
T. Rajale, Sh. Sharma, D. Stroud, D. K. Unruh, E. Miaou, K. Lai, and D. M. Birney, Tetrahedron Lett., 55, 6627 (2014).
S. Combes, P. Barbier, S. Douillard, A. McLeer-Florin, V. Bourgarel-Rey, J.-Th. Pierson, A. Yu. Fedorov, J.-P. Finet, J. Boutonnat, and V. Peyrot, J. Med. Chem., 54, 3153 (2011).
Ch. Radanyi, G. Le Bras, and S. Messaoudi, Bioorg. Med. Chem. Lett., 18 (7), 2495 (2008).
J.-T. Pierson, A. Dumetre, S. Hutter, F. Delmas, M. Laget, J.-P. Finet, N. Azas, and S. Combes, Eur. J. Med. Chem., 45, 864 (2010).
P. Mutai, G. Breuzard, A. Pagano, D. Allergo, V. Peyrot, and K. Chibale, Bioorg. Med. Chem., 25 (5), 1652 (2017).
Li Xu, B.-J. Li, Z.-H. Wu, X.-Yu Lu, B.-T. Guan, B.-Q. Wang, Ke-Q. Zhao, and Zh.-J. Shi, Org. Lett., 12 (4), 884 (2010).
Yu. B. Malysheva, Yu. V. Voitovich, E. A. Sharonova, S. Combes, E. V. Svirshchevskaya, E. L. Vodovozova, and A. Yu. Fedorov, Russ. Chem. Bull., 62 (4), 1103 (2013).
N. S. Sitnikov, A. S. Shavyrin, G. K. Fukin, I. P. Beletskaya, S. Combes, and A. Yu. Fedorov, Russ. Chem. Bull., 59 (3), 626 (2010).
O. A. Akrawi, G. Z. Nagy, T. Patonay, A. Villinger, and P. Langer, Tetrahedron Lett., 53, 3206 (2012).
Z. Khaddour, O. A. Akrawi, A. S. Suleiman, T. Patonay, A. Villinger, and P. Langer, Tetrahedron Lett., 55 (32), 4421 (2014).
P. G. Ciattini, E. Morera, and G. Ortar, Synth. Commun., 25 (18), 2883 (1995).
S. Wattanasin, Synth. Commun., 18 (16–17), 1919 (1988).
A. M. El-Agrody, A. H. Bedair, F. M. Aly, and F. A. Abu-Shanab, J. Chem. Soc. Pak., 15 (4), 261 (1993).
J. Wu, Y. Liao, and Zh. Yang, J. Org. Chem., 66 (10), 3642 (2001).
J. Wu and Zh. Yang, J. Org. Chem., 66 (23), 7875 (2001).
D. M. X. Donnelly, J. P. Finet, P. J. Guiry, and R. M. Hutchinson, J. Chem. Soc., Perkin Trans. 1, No. 10, 2851 (1990).
R. D. Rieke and S.-H. Kim, Tetrahedron Lett., 52 (24), 3094 (2011).
L. Schio, F. Chatreaux, and M. Klich, Tetrahedron Lett., 41 (10), 1543 (2000).
M. L. N. Rao, V. Venkatesh, and D. N. Jadhav, Eur. J. Org. Chem., 3945 (2010).
M. L. N. Rao and A. Kumar, Tetrahedron, 70, 6995 (2014).
M. L. N. Rao and A. Kumar, Tetrahedron, 71, 5137 (2015).
J.-G. Lei, M.-H. Xu, and G.-Q. Lin, Synlett, 13, 2364 (2004).
M. Khoobi, M. Alipour, S. Zarei, F. Jafarpour, and A. Shafiee, Chem. Commun., 48, 2985 (2012).
S. F. Motevalizadeh, M. Alipor, F. Ashori, A. Samzadeh-Kermani, H. Hamadi, M. R. Ganjali, H. Aghahosseini, A. Ramazan, M. Khoobi, and E. Gholibegloo, Appl. Organomet. Chem., 32 (3), e4123 (2017).
Y. Li, Z. Qi, H. Wang, X. Fu, and Ch. Duan, J. Org. Chem., 77, 2053 (2012).
M. Min and S. Hong, Chem. Commun., 48, 9613 (2012).
S.-R. Li, L.-Y. Chen, J.-Ch. Tsai, et al., Tetrahedron Lett., 48 (12), 2139 (2007).
A. Patra and S. K. Misra, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 29 (1), 66 (1990).
M. Natarajan, T. Manimaran, and V. T. Ramakrishnan, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 23 (6), 529 (1984).
Sh. Ren, J. Zhang, J. Zhang, H. Wang, W. Zhang, Yu. Liu, and M. Liu, Eur. J. Org. Chem., 5381 (2015).
H. Sun, Y. Zhang, F. Guo, Y. Yan, Ch. Wan, Zh. Zha, and Zh. Wang, Eur. J. Org. Chem., 480 (2012).
J. Banothu, R. Velpula, R. Gali, R. Bavantula, and P. A. Crook, Tetrahedron Lett., 54 (29), 3862 (2013).
L. Fang, L. Xue, P. Yang, X. Li, and Zh. Wang, Chem. Lett., 46 (8), 1223 (2017).
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Translated from Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2019, pp. 341–365.
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Moskvina, V.S., Khilya, V.P. Recent Progress in the Synthesis of 4-Arylcoumarins. Chem Nat Compd 55, 401–427 (2019). https://doi.org/10.1007/s10600-019-02705-8
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DOI: https://doi.org/10.1007/s10600-019-02705-8