Stereoselective Synthesis of cis-Substituted-3’-anilino-2’, 3’-dihydro-4-2’-benzo[b]furanylcoumarins via Intramolecular Aldol Reactions

Abstract

The present study reports the reaction of 4-bromomethylcoumarins with salicylidineaniline in acetone with two equivalents of potassium carbonate resulted in the formation of title compounds at room temperature via intramolecular aldolization. The obtained compound is thermodynamically and kinetically stable with highly stereoselective and excellent yield.

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L. A. Shastri, S. L. Shastri, M. V. Kulkarni, V. K. Gupta and S. Goswami, "Stereoselective Synthesis of cis-Substituted-3’-anilino-2’, 3’-dihydro-4-2’-benzo[b]furanylcoumarins via Intramolecular Aldol Reactions," International Journal of Organic Chemistry, Vol. 2 No. 1, 2012, pp. 44-48. doi: 10.4236/ijoc.2012.21008.

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1] A. A. Ali, M. H. Mohamed, M. S. Kamel and M. A. Fouad, “Spring Studies on Securigera securidacea (L.) Deg. Dorfl. (Fabaceae) Seeds, an Antidiabetic Egyptian Folk Medicine,” Pharmazie, Vol. 53, 1998, pp. 710-715.
[2] K. Kataoka, T. Shiota, T.Takumi, T. Minoshima, W. Kenzo, T. Hiroko, M. Tsutomu, T. Keiko, O. Mikio, T. Hirofumi and Y. Hisao, “Potent Inhibitors of Acyl-CoA: Cholesterol Acyltransferase. 2. Structure-Activity Relationships of Novel N-(2,2-Dimethyl- 2,3-dihydro-benzo- furan-7-yl)amides,” Journal of Medicinal Chemistry, Vol. 39, No.8, 1996, pp. 1262-1270. doi:10.1021/jm950828+
[3] P. M. Aaron, R. W. Steve, M. L. Danuta, B. W. David, L. N. David, S. B. Elaine and E. N. David, “Dihydrobenzofuran Analogues of Hallucinogens. 4.1 Mescaline Derivatives,” Journal of Medicinal Chemistry, Vol. 40, No. 19, 1997, pp. 2997-3008. doi:10.1021/jm970219x
[4] U. Bhoga, “A New Synthetic Approach to Enantiomerically Enriched Dihydrobenzofurans: Use of a Hydrolytic Kinetic Resolution and an Intramolecular Epoxide Ring Opening Protocol Using 1-Benzyloxy-2-oxiranylmethyl- benzenes,” Tetrahedron Letters, Vol. 46, No. 31, 2005, pp. 5239-5242. doi:10.1016/j.tetlet.2005.04.120
[5] S. H. Shrikant, V. K. Manohar and D. P. Vemanna, “Synthesis and Biological Activity of 4-(Sulphona Midomethyl) Coumarins,” Indian Journal of Chemistry, Vol. 24 B, 1985, pp. 459-461.
[6] J. G. Finn, E. Kenealy, S. Creaven and D. S. Egan, “In Vitro Cytotoxic Potential and Mechanism of Action of Selected Coumarins, Using Human Renal Cell Lines,” Cancer Letters, Vol. 183, No. 1, 2002, pp. 61-68. doi:10.1016/S0304-3835(02)00102-7
[7] S. A. Khanum, S. Shashikanth, B. S. Sudha and S. N. Sriharsha, “Photochemical Synthesis, and Antimicrobial Activity of Dihydrobenzofuranols from 2-Alkoxy Substituted Benzophenones and Ethyl-2-Aroyl Aryloxy Acetates,” Journal of Chemical Research, Vol. 8, 2003, pp. 463-464. doi:10.3184/030823403103174830
[8] Z. Yefen, L. Mercedes and B. S. Barry, “Synthesis of 2, 3-Dihydro-3-hydroxy-2-hydroxylalkylbenzofurans from Epoxy Aldehydes. One-Step Syntheses of Brosimacutin G, Vaginidiol, Vaginol, Smyrindiol, Xanthoarnol, and Avicenol A. Biomimetic Syntheses of Angelicin and Psoralen,” Journal of Organic Chemistry, Vol. 70, No. 5, 2005, pp. 1761-1770. doi:10.1021/jo047974k
[9] L. John, H. Svend and T. Ole, “Dihydrofurocoumarin Glucosides from Angelica Archangelica and Angelica Silvestris,” Phytochemistry, Vol. 22, No. 2, 1983, pp. 553-555. doi:10.1016/0031-9422(83)83044-1
[10] J. Benedicto, C. G. Maria, A. Josefa, T. Pascual and G. Manuel, “Coumarins from Ferulago capillaris and F. Brachyloba,” Phytochemistry, Vol. 53, No. 8, 2000, pp. 1025-1031. doi:10.1016/S0031-9422(99)00524-5
[11] D. G. Bishan, K. B. Sunil and K. L Hand, “Alkaloids and coumarins of Heracleum wallichii,” Phytochemistry, Vol. 15, No. 4, 1976, pp. 576-576. doi:10.1016/S0031-9422(00)88988-8
[12] S. Hiroko, S. Yuta-ka, N. Hiroyuki and K. J. Yoko, “Plant Growth Regulators from Heracleum Lanatum,” Phytochemistry, Vol. 21, No. 9, 1982, pp. 2213-2215. doi:10.1016/0031-9422(82)85180-7
[13] Y. Kwase, S. Yama-guchi, S. Kondo and K. Shimokawa, “The Synthesis of dl-5-Acetyl-2-(1-hydrxymethylvi- nyl)-2,3-dihydrobenzofuran and Its Esters,” Chemistry Letters, Vol. 7, No. 3, 1978, pp. 253-254. doi:10.1246/cl.1978.253
[14] H. Takahiro, U. Tetsuyuki and S. Murahashi, “Ichi. Palladium(II)-Catalysed Oxidative Cyclisation of 2-Allylph-enols in the Presence of Copper(II) Acetate and Molecular Oxygen. Oxidation State of Palladium in the Wacker-Type Reaction,” Journal of the Chemical Society, Chemical Communications, No. 11, 1979, pp. 475-476.
[15] R. Rastogi, G. Dixit and K. Zutshi, “Electrochemical Synthesis of Benzofuroxan: Role of Electrogenerated Iodonium Ion in the Intramolecular Cyclization of 2-Ni- troaniline,” Electrochimica Acta, Vol. 29, No. 10, 1984, pp. 1345-1347. doi:10.1016/0013-4686(84)87008-5
[16] B. Raymond, G. C. Nigel, R. H. Guy, H. B. W. Stanley and H. Jordan, “Stereoselective Synthesis of the Dihydrobenzo[b]furan Seg-ments of the Ephedradine Alkaloids,” Journal of the Chemical Society, Chemical Communications, No. 14, 1987, pp. 1102-1104.
[17] M. A. Huffman and L. S. Liebeskind, “Nick-el(0)-Cata- lyzed Synthesis of Substituted Phenols from Cyc-lobutenones and Alkynes,” Journal of the American Chemical Society, Vol. 113, No. 7, 1991, pp. 2771-2772. doi:10.1021/ja00007a072
[18] S. Olivero, J. C. Clinet and J. C. E. Dunach, “Electrochemical Intramolecular Reductive Cyclisation Catalysed by Electrogenerated Ni(cyclam)2,” Tetrahedron Letters, Vol. 36, No. 25, 1995, pp. 4429-4432. doi:10.1016/0040-4039(95)00782-8
[19] K. Chiba, M. Fukuda, S. Kim, Y. Kitano and M. Ta da, “Dihydrobenzofuran Synthesis by an Anodic [3 + 2] Cycloaddition of Phenols and Unactivated Al Kenes,” Journal of Organic Chemistry, Vol. 64, No. 20, 1999, pp. 7654-7656. doi:10.1021/jo9908243
[20] R. Mahrwald, “Diastereoselection in Lewis-Acid-Medi-ated Aldol Additions,” Chemical Reviews, Vol. 99, No. 5, 1999, pp. 1095-1120. doi:10.1021/cr980415r
[21] R. Mahrwald, “Modern Aldol Reactions,” Wiley-VCH, Weinheim, 2004. doi:10.1002/9783527619566
[22] C. Palomo, M. Oiarbide and J. M. Garcia, “Current Progress in the Asymmetric Aldol Addition Reaction,” Chemical Society Reviews, Vol. 33, No. 2, 2004, pp. 65-75. doi:10.1039/b202901d
[23] D. Enders, O. Niemeier and L. Straver, “Asymmetric Organocatalytic Synthesis of cis-Substituted-Dihydro- benzofuranols via Intramolecular Aldol Reactions,” Synlett, No. 20, 2006, pp. 3399-3402. doi:10.1055/s-2006-956454
[24] J. Arumugasamy and L. Yong-Chien, “Indium-Mediated Tandem Dimerization and Cyclization of Nitrqones and Aldimines to 3-Arylaminodihydrobenzofurans under Aqueous Conditions,” Tetrahedron Letters, Vol. 42, No. 25, 2001, pp. 4361-4362. doi:10.1021/jo980601x
[25] J. Yoshida, M. Sugawara, M. Tatsumi and N. Kise, “Electrooxidative Inter and Intramolecular Carbon-Carbon Bond Formation Using Organothio Groups as Electroauxiliaries,” Journal of Organic Chemistry, Vol. 63, No. 17, 1998, pp. 5950-5961.
[26] M. L. Kerns, S. M. Conroy and J. S. Swenton, “Dihydrobenzofuran Derivatives via the Anodic Cycloaddition Reaction of p-Methoxyphenols and Vinyl Sulfides,” Tetrahedron Letters, Vol. 35, No. 41, 1994, pp. 7529-7532. doi:10.1016/S0040-4039(00)78335-3
[27] U. Bhoga, “A New Synthetic Approach to Enantiomerically Enriched Dihydro-benzofurans: Use of a Hydrolytic Kinetic Resolution and an Intramolecular Epoxide Ring Opening Protocol Using 1-Benzyloxy-2-oxiranylmethy- lbenzenes,” Tetrahedron Letters, Vol. 46, No. 31, 2005, pp. 5239-5242. doi:10.1016/j.tetlet.2005.04.120
[28] S. P. Pappas, D. Z. Robert and E. A. James, “On Vicinal H-H Coupling Constants in 3-Hydroxy-2,3-dihydroben- zofuran Derivatives,” Journal of Heterocyclic Chemistry, Vol. 7, No. 5, 1970, pp. 1215-1217. doi:10.1002/jhet.5570070541
[29] E. M. Sharshira, S. Shimada, M. O. E. Hasegawa and T. Horaguchi, “Photocyclization reactions. Part-5. Synthesis of Dihydrobenzofuranols Using Photocyclization of 2- Alkoxybenzophenones and Ethyl 2-Benzoylphenoxyacetates,” Journal of Heterocyclic Chemistry, Vol. 33, 1996, pp. 1797-1805. doi:10.1002/jhet.5570330641
[30] P. J. Wagner, M. A. Meador and B. S. Park, “The Photocyclization of O-Alkoxy Phenyl Ketones,” Journal of the American Chemical Society, Vol. 112, No. 13, 1990, pp. 5199-5211. doi:10.1021/ja00169a031
[31] P. J. Wagner and J. S. Jang, “Lifetimes of 1,5-Biradicals Formed from Triplet O-Alkoxy Ketones,” Journal of the American Chemical Society, Vol. 115, No. 17, 1993, pp. 7914-7915. doi:10.1021/ja00070a062
[32] P. J. Wagner, M. A. Meador and J. C. Seaiano, “Photocyclizations of O-(Benzyloxy)acetophenone and -Benzo-phenone: Effects of Variable Rotational Freedom on Biradical Behavior,” Journal of the American Chemical Society, Vol. 106. No. 25, 1984, pp. 7988-7989. doi:10.1021/ja00337a066
[33] M. Abdul-Aziz, J. V. Auping and M. A. Meador, “Synthesis of Substi-tuted-2,3,5,6-tetraarylbenzo[1,2,-b: 4,5-b'] Difurans,” Journal of Organic Chemistry, Vol. 60, No. 5, pp. 1303-1308. doi:10.1021/jo00110a038
[34] M. A. Meador and P. J. Wagner, “Photocyclization of Alpha. (O-Benzyloxyphenyl) Acetophe-none: Triplet-State Epsilon-Hydrogen Abstraction,” Journal of Organic Chemistry, Vol. 50, No. 3, 1985, pp. 419-420. doi:10.1021/jo00203a038
[35] S. S. Hanmanthgad, V. D. Patil, V. D. Prakash, R. K. Dhruvaraj and V. M. Kulkarni, “Synthesis and Pharmacological Properties of Same 4, 2’-[Benzo(b)furanyl] Coumarins,” Indian Journal of Chemistry, Vol. 25B, 1986, pp. 779-781.
[36] L. A. Shastri, M. V. Kulkarni, V. K. Gupta and S. Gos- wami, “First Thermal Chemoselective Synthesis of Novel 20,30-Dihydro-30-Hydroxybenzo Furanylcoumarins,” Synthetic Communications, Vol. 38, 2008, pp. 1407-1415. doi:10.1080/00397910801914251
[37] M. V Kulkarni and V. D. Patil, “Studies on Coumarins,” Arch Pharm. (Weinheim), Vol. 314, 1981, pp. 708-711. doi:10.1002/ardp.19813140810

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