Citation:
Tariq Mahmood Babar, Muhammad Moazzam Naseer, Muhammad Khawar Rauf, Humayun Pervez, Masahiro Ebihara, Nasim Hasan Rama. Synthesis of hexacyclic fused isocoumarin framework through selective domino multicyclizations under catalyst and solvent free conditions[J]. Chinese Chemical Letters,
;2014, 25(9): 1282-1286.
doi:
10.1016/j.cclet.2014.03.022
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A novel fused isocoumarin skeleton has been synthesized through selective domino multicyclizations by mixing homothallic acid and 2,3-diphenylacryloyl chloride at 200℃ under catalyst and solvent free reaction conditions. Six fused rings with two stereogenic centers were assembled in a convenient onepot operation in good yield. The resulting hexacyclic fused isocoumarin skeleton and its stereochemistry was fully characterized and unambiguously confirmed by X-ray diffraction analysis.
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Keywords:
- Hexacyclic,
- Fused isocoumarin,
- One pot,
- Catalyst and solvent free
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[1]
[1] (a) G.L. Adams, P.J. Carroll, A.B. Smith, Access to the Akuammiline family of alkaloids: total synthesis of (+)-scholarisine A, J. Am. Chem. Soc. 135 (2013) 519-528; (b) W. Fan, Q. Ye, H.W. Xu, et al., Novel double [3+2+1] heteroannulation for forming unprecedented dipyrazolo-fused 2,6-naphthyridines, Org. Lett. 15 (2013) 2258-2261; (c) B. Jiang, X. Wang, H.W. Xu, et al., Highly selective domino multicyclizations for forming polycyclic fused acridines and azaheterocyclic skeletons, Org. Lett. 15 (2013) 1540-1543; (d) M. Piltan, I. Yavari, L. Moradi, Tandem synthesis of functionalized hexaalkyl benzoisoquinolinopyrrolonaphthyridine-hexacarboxylate, via isoquinoline based multi-component reaction, Chin. Chem. Lett. 24 (2013) 979-983; (e) A.D. Melhado, W.E. Brenzovich, A.D. Lackner, F.D. Toste, Gold-catalyzed threecomponent coupling: oxidative oxyarylation of alkenes, J. Am. Chem. Soc. 132 (2010) 8885-8887; (f) R.A. Yoder, J.N. Johnston, A case study in biomimetic total synthesis: polyolefin carbocyclizations to terpenes and steroids, Chem. Rev. 105 (2005) 4730-4756.
-
[2]
[2] (a) P.C. Chao, C.C. Hsu, M.C. Yin, Anti-inflammatory and anti-coagulatory activities of caffeic acid and ellagic acid in cardiac tissue of diabetic mice, Nutr. Metab. 6 (2009) 33; (b) G. Cozza, A. Gianoncelli, P. Bonvini, et al., Urolithin as a converging scaffold linking ellagic acid and coumarin analogues: design of potent protein kinase CK2 inhibitors, ChemMedChem 6 (2011) 2273-2286; (c) H.A. De Abreu, I.A.D.S. Lago, G.P. Souza, et al., Antioxidant activity of (+)-bergenin -a phytoconstituent isolated from the bark of Sacoglottis uchi Huber (Humireaceae), Org. Biomol. Chem. 6 (2008) 2713-2718; (d) J.H. Weisburg, A.G. Schuck, S.E. Reiss, et al., Ellagic acid, a dietary polyphenol, selectively cytotoxic to HSC-2 oral carcinoma cells, Anticancer Res. 33 (2013) 1829-1836; (e) T.Y. Kao, Y.C. Chung, Y.C. Hou, et al., Effects of ellagic acid on chemosensitivity to 5-fluorouracil in colorectal carcinoma cells, Anticancer Res. 32 (2012) 4413-4418; (f) Y.S. Kim, T. Zerin, H.Y. Song, Antioxidant action of ellagic acid ameliorates paraquat-induced A549 cytotoxicity, Biol. Pharm. Bull. 36 (2013) 609-615.
-
[3]
[3] (a) F. Nemati, R. Saeedirad, Nano-Fe3O4 encapsulated-silica particles bearing sulfonic acid groups as a magnetically separable catalyst for green and efficient synthesis of functionalized pyrimido[4,5-b]quinolines and indeno fused pyrido[ 2,3-d]pyrimidines in water, Chin. Chem. Lett. 24 (2013) 370-372; (b) W.C. Gong, Y. Liu, J. Zhang, et al., Regio-and stereoselective [4+3] cycloaddition towards fused 5,7,6-tricyclic skeletons, Chem. Asian J. 8 (2013) 546-551; (c) S. Yasuike, M. Niwa, K. Yamaguchi, T. Tsuchiya, J. Kurita, Synthesis of 1-stibaphenalenes, the first example of group 15 phenalenes, via a 1,5-dilithium intermediate, Chem. Lett. 30 (2001) 554-555; (d) J.J. Kaloko, Y.H. Gary, T.I. Ojima, One-step formation of fused tetracyclic skeletons from cyclohexene-diynes and carbon monoxide through Rh(I)-catalyzed[2+2+2+1] cycloaddition reaction, Chem. Commun. (2009) 4569-4571; (e) H. Mizoguchi, H. Oguri, K. Tsuge, H. Oikawa, Divergent and expeditious access to fused skeletons inspired by indole alkaloids and transtaganolides, Org. Lett. 11 (2009) 3016-3019; (f) N. Saito, T. Ichimaru, Y. Sato, Ruthenium-catalyzed intramolecular [2+2+2] cyclization of allene-yne-enes: construction of fused-tricyclic skeletons, Chem. Asian J. 7 (2012) 1521-1523; (g) S. Rostamizadeh, M. Nojavan, R. Aryan, H. Sadeghian, M. Davoodnejad, A novel and efficient synthesis of pyrazolo[3,4-d]pyrimidine derivatives and the study of their anti-bacterial activity, Chin. Chem. Lett. 24 (2013) 629-632; (h) F. Shi, X.N. Zeng, X.D. Cao, et al., Design and diversity-oriented synthesis of novel 1,4-thiazepan-3-ones fused with bioactive heterocyclic skeletons and evaluation of their antioxidant and cytotoxic activities, Bioorg. Med. Chem. Lett. 22 (2012) 743-746.
-
[4]
[4] (a) A. Ahmed, S. Dhara, J.K. Ray, Palladium-catalyzed and (KOBu)-Bu-t-promoted C-aryl-O-alcoholic coupling: an efficient one-pot synthesis of oxygen containing fused rings, Tetrahedron Lett. 54 (2013) 1673-1676; (b) P. Sang, M. Yu, H.F. Tu, J.W. Zou, Y.H. Zhang, Highly regioselective synthesis of fused seven-membered rings through copper-catalyzed cross-coupling, Chem. Commun. 49 (2013) 701-703; (c) A. Caruso, M.A. Siegler, J.D. Tovar, Synthesis of functionalizable boron-containing pi-electron materials that incorporate formally aromatic fused borepin rings, Angew. Chem. Int. Ed. 49 (2010) 4213-4217; (d) M.A. Esteruelas, I. Fernandez, A. Herrera, et al., Multiple C-H bond activation of phenyl-substituted pyrimidines and triazines promoted by an osmium polyhydride: formation of osmapolycycles with three, five, and eight fused rings, Organometallics 29 (2010) 976-986; (e) D.R. Levine, A. Caruso, M.A. Siegler, J.D. Tovar, Meta-B-entacenes: new polycyclic aromatics incorporating two fused borepin rings, Chem. Commun. 48 (2012) 6256-6258; (f) S. Maiti, M.G.B. Drew, R. Mukhopadhyay, B. Achari, A.K. Banerjee, Convenient formation of six-to nine-membered carbocyclic rings by 2-pyridyl radical cyclization: a generalized synthesis of pyridine-fused linear tricyclic systems, Synthesis-Stuttgart (2005) 3067-3078; (g) K. Niimi, S. Shinamura, I. Osaka, E. Miyazaki, K. Takimiya, Dianthra[2,3-b:2030-f]thieno[3,2-b]thiophene (DATT): synthesis, characterization, and FET characteristics of new π-extended heteroarene with eight fused aromatic rings, J. Am. Chem. Soc. 133 (2011) 8732-8739; (h) V. Novakova, J. Roh, P. Gela, J. Kunes, P. Zimcik, Azaphthalocyanines with fused triazolo rings: formation of sterically stressed constitutional isomers, Chem. Commun. 48 (2012) 4326-4328; (i) L.A. Paquette, R.V.C. Carr, E. Arnold, J. Clardy, Electronic control of stereoselectivity. 5. Stereochemistry of singlet oxygen capture by cyclopentadiene rings fused to norbornyl and norbornenyl frameworks, J. Org. Chem. 45 (1980) 4907-4913.
-
[5]
[5] (a) D. Du, Z.W. Wang, N-Heterocyclic carbene-catalyzed domino reactions of formylcyclopropane 1,1-diesters: a new synthesis of coumarins, Eur. J. Org. Chem. (2008) 4949-4954; (b) M.A. Kinder, P. Margaretha, Photochemistry of 4H,7H-benzo[1,2-c: 4,3-c0]dipyran-4,7-dione, a twofold isocoumarin, Org. Lett. 2 (2000) 4253-4255; (c) V. Nair, C.R. Sinu, R. Rejithamol, K.C.S. Lakshmi, E. Suresh, A novel NHCcatalyzed transformation of 2H-chromene-3-carboxaldehydes to 3-methyl-2Hchromen-2-ones, Org. Biomol. Chem. 9 (2011) 5511-5514; (d) S. Ozcan, M. Balci, The chemistry of homophthalic acid: a new synthetic strategy for construction of substituted isocoumarin and indole skeletons, Tetrahedron 64 (2008) 5531-5540; (e) E.M. Phillips, M. Wadamoto, H.S. Roth, A.W. Ott, K.A. Scheidt, NHC-catalyzed reactions of aryloxyacetaldehydes: a domino elimination/conjugate addition/acylation process for the synthesis of substitutedcoumarins,Org. Lett.11(2009) 105-108; (f) S.P. Waters, M.C. Kozlowski, Synthesis of the isocoumarin portion of the rubromycins, Tetrahedron Lett. 42 (2001) 3567-3570.
-
[6]
[6] (a) F. Borges, F. Roleira, N. Milhazes, L. Santana, E. Uriarte, Simple coumarins and analogues in medicinal chemistry: occurrence, synthesis and biological activity, Curr. Med. Chem. 12 (2005) 887-916; (b) R. O'Kennedy, R.D. Thornes, Coumarins: Biology, Applications, and Mode of Action, Wiley, Chichester, NY, 1997; (c) M.E. Riveiro, N. de Kimpe, A. Moglioni, et al., Coumarins: old compounds with novel promising therapeutic perspectives, Curr. Med. Chem. 17 (2010) 1325-1338.
-
[7]
[7] S. Vilar, E. Quezada, L. Santana, et al., Design, synthesis, and vasorelaxant and platelet antiaggregatory activities of coumarin-resveratrol hybrids, Bioorg. Med. Chem. Lett. 16 (2006) 257-261.
-
[8]
[8] O. Thastrup, J.B. Knudsen, J. Lemmich, K. Winther, Inhibition of human-platelet aggregation by dihydropyrano and dihydrofuranocoumarins, a new class of camp-phosphodiesterase inhibitors, Biochem. Pharmacol. 34 (1985) 2137-2140.
-
[9]
[9] D.L. Yu, M. Suzuki, L. Xie, S.L. Morris-Natschke, K.H. Lee, Recent progress in the development of coumarin derivatives as potent anti-HIV agents, Med. Res. Rev. 23 (2003) 322-345.
-
[10]
[10] (a) E. Budzisz, E. Brzezinska, U. Krajewska, M. Rozalski, Cytotoxic effects, alkylating properties and molecular modelling of coumarin derivatives and their phosphonic analogues, Eur. J. Med. Chem. 38 (2003) 597-603; (b) D. Cooke, R. O'Kennedy, Comparison of the tetrazolium salt assay for succinate dehydrogenase with the cytosensor microphysiometer in the assessment of compound toxicities, Anal. Biochem. 274 (1999) 188-194; (c) D. Egan, P. James, D. Cooke, R. OKennedy, Studies on the cytostatic and cytotoxic effects and mode of action of 8-nitro-7-hydroxycoumarin, Cancer Lett. 118 (1997) 201-211; (d) P. Hilgard, R.D. Thornes, Perspectives in cancer research anticoagulants in treatment of cancer, Eur. J. Cancer 12 (1976) 755-762; (e) U.S. Weber, B. Steffen, C.P. Siegers, Antitumor-activities of coumarin, 7-hydroxy-coumarin and its glucuronide in several human tumor cell lines, Res. Commun. Mol. Path. 99 (1998) 193-206.
-
[11]
[11] C.A. Kontogiorgis, K. Savvoglou, D.J. Hadjipavlou-Litina, Antiinflammatory and antioxidant evaluation of novel coumarin derivatives, J. Enzym. Inhib. Med. Chem. 21 (2006) 21-29.
-
[12]
[12] (a) H.S. Jung, P.S. Kwon, J.W. Lee, et al., Coumarin-derived Cu2+-selective fluorescence sensor: synthesis, mechanisms, and applications in living cells, J. Am. Chem. Soc. 131 (2009) 2008-2012; (b) X.G. Liu, J.M. Cole, P.G. Waddell, et al., Molecular origins of optoelectronic properties in coumarin dyes: toward designer solar cell and laser applications, J. Phys. Chem. A 116 (2012) 727-737.
-
[13]
[13] H. Kaji, M. Yamada, K. Nozawa, K. Kawai, S. Nakajima, Synthesis of antifungal isocoumarins, Org. Prep. Proced. Int. 18 (1986) 253-262.
-
[14]
[14] (a) S.J. Cai, F. Wang, C.J. Xi, Assembly of 3-substituted isocoumarins via a Culcatalyzed domino coupling/addition/deacylation process, J. Org. Chem. 77 (2012) 2331-2336; (b) T.L. Yao, R.C. Larock, Synthesis of isocoumarins and alpha-pyrones via electrophilic cyclization, J. Org. Chem. 68 (2003) 5936-5942.
-
[15]
[15] (a) K. Katsumoto, C. Kitamura, T. Kawase, An indenone synthesis involving a new aminotransfer reaction and its application to dibenzopentalene synthesis, Eur. J. Org. Chem. (2011) 4885-4891; (b) R. Leardini, D. Nanni, A. Tundo, G. Zanardi, Novel [3+2] radical annulations of cyano-substituted aryl radicals with alkynes, Tetrahedron Lett. 39 (1998) 2441-2442.
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