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Benzofuran Synthesis Through Iodocyclization Reactions: Recent Advances MOJ Bioorganic & Organic Chemistry Mini Review Open Access Benzofuran synthesis through iodocyclization reactions: recent advances Abstract Volume 1 Issue 7 - 2017 Recent advancements (2014-17) in the benzofuran synthesis through iodocyclization Saurabh Mehta have been summarized. The successful use of various iodinating agents, bases, additives Department of Applied Chemistry, Delhi Technological etc. make iodocyclization a versatile and efficient methodology. The methodology has University, India been applied for the synthesis of more complex benzofuran derivatives, and may open interesting avenues in the area of heterocyclic chemistry (Figure 1). Correspondence: Saurabh Mehta, Department of Applied O-LG Chemistry, Delhi Technological University, Bawana Road, Delhi, + O R1 I 1 2 110042 India, Tel +9188 0066 5868, R R Email [email protected], [email protected] R2 I Received: December 17, 2017 | Published: December 29, 2017 LG = H, Me or other Protecting group 1 R = H, Me, OMe, I, CO2Me, etc. R2 = H, aryl, alkyl, alkenyl, etc. Figure 1 Keywords: annulations, alkyne, benzofuran, iodocyclization, heterocycle Introduction derivatives were obtained in high yields (84%−100%) under mild conditions. The authors demonstrated that the choice of bis(2,4,6- Benzo[b]furan is a privileged heterocyclic scaffold. Several collidine)iodonium hexafluorophosphate [I(coll)2PF6] as the compounds containing this scaffold have interesting biological iodinating agent was necessary for the success of the reaction. Also, 1 activities, such as anti-cancer, anti-viral, anti-inflammatory, etc. Few the ethoxyethyl ether group acted as a protecting group as well as a 2 derivatives are even used as commercial drugs, such as Amiodarone, good leaving group. 3 or investigational drugs, such as Bufuralol, etc. (Figure 2). EWG N I R2 I(coll) PF EWG O 2 6 1 R1 R N DCM, rt O R2 O OH O I O 3 seconds EWG = Ts, etc. NH OEt 1 R = H, Ph, OMe, NO2, etc. O N I R2 = Me, Bn, ring, etc. Amiodarone Bufuralol (Antiarrhythmic agent) (ß-Adrenergic blocker) Scheme 1 Figure 2 Examples of Benzo[b]furan scaffold containing drugs. The authors used a similar and previously reported methodology12 Over the years many synthetic routes have been reported for the for the synthesis (Scheme 2) of an antiarrhythmic agent Dronedarone ® 13 preparation of benzofurans.1,4,5 Iodocyclization of functionalized (marketed as Multaq from Sanofi-Aventis). OEt alkynes is one of the most important and efficient synthetic (i) I(coll)2PF6, BF3·OEt2 I nBu CH Cl methodologies for the synthesis of important heterocyclic compounds, O 2 2 O N r.t., 10 min n 6,7 nBu B including benzofurans. Due to our continuous interest in the Ms (ii) 10% HCl, u N O (HO) B 8–10 THF, MeOH 2 synthesis and biological evaluation of important heterocycles, we nBu 77% (2 steps) OEt 60°C, 30 min PdCl2(PPh3)2, K2CO3 became interested in Benzofuran synthesis. Here the recent advances CO (1 atm) (2014-17) in this powerful strategy for making benzofurans are anisole reported. 80°C, 23 h O O nBu N Discussion nBu nBu Okitsu et al.11 recently reported a versatile synthesis of benzo[b] O Dronedarone furans through iodocyclization of the ethoxyethyl ether-substituted 57% 11 alkynes (Scheme 1). The reactions get completed within three Scheme 2 seconds at room temperature and the corresponding benzofuran Submit Manuscript | http://medcraveonline.com MOJ Biorg Org Chem. 2017;1(7):262‒264. 262 © 2017 Mehta. This is an open access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and build upon your work non-commercially. Copyright: Benzofuran synthesis through iodocyclization reactions: recent advances ©2017 Mehta 263 14 Wang et al. developed a novel and straightforward involves the iodocyclization of alkynylated 2-iodoanisoles using I2 in way for the preparation of 3-trifluoromethylbenzofurans.14 the presence of sodium bicarbonate as base (Scheme 8). The resulting The methodology involves a two-step, one-pot tandem products containing two C-I bonds offer opportunities for further iodocyclization and trifluoromethylation reaction and affords the diversification of this important scaffold. 3-trifluoromethylbenzofurans in moderate to excellent yields (Scheme R3 O 3). OMe OMe ICl PdCl (PPh ) , CuI 1 2 O 2 3 2 R R B(OH)2 DCM 1 Et NH OMe R 2 R2 1 o 2 rt, 4 h 2 R (i) 1 equiv I2, 40 C O Br Suzuki coupling R R DMF R1 1 R1 41-93% R I 80 °C, 15 h (ii) TMSCF3/KF/CuI R2 30-89% o 3 2 DMF, 100 C R R CF3 49-81% Scheme 6 R1 = H, Cl, F, OMe, Ph, alkyl, etc. O OMe Zn HO OMe TsO O R2 = H, Cl, F, OMe, alkyl, CO Me, CN, (i) TsCl, TEA 2 etc. AcOH/H2O R Scheme 3 (ii) I2, NaHCO3 OH I R R 56-100% Danilkina et al.15 reported an efficient strategy for the synthesis R = alkyl, aryl, alkenyl, etc. of asymmetrically substituted enediynes fused to benzofuran, and other important heterocycles (Scheme 4).15 The authors also Scheme 7 demonstrated the extension of the methodology for the synthesis of I I fused macrocycles of indole derivatives. OMe 3.0 I2 3.0 NaHCO O OMe Cu/Pd O 3 R2 O R Ph 1 DCE I2 R 1 Ph 70 oC, 24h R R2 I R1 = H, Cl, Me I R = TMS, hexyl, etc. 45-99% 2 Ph R R = alkyl, aryl Scheme 4 Scheme 8 Li et al.16 demonstrated that a variety of 3-iodobenzo[b]furan Conclusion derivatives can be conveniently prepared from the corresponding Thus, the iodocyclization strategy presents an efficient approach 2-alkynylphenols through Ph3P-catalyzed iodocyclization in the presence of N-iodosuccinimide (NIS).16 This protocol provides a for the synthesis of diverse benzo [b] furan derivatives. The choice of quick access to and 3-iodobenzo[b]furans in good to excellent yields reagents, fast and high yielding reactions combined with the functional under mild conditions (Scheme 5). group tolerance make it a strategy of choice for many heterocyclic NIS (2.0 equiv) chemists. Further advances in this area of research are expected. OH O R1 Ph3P (0.1 equiv) R1 R2 Acknowledgements DCE, rt The author thanks Delhi Technological University for the resources 2 R I provided for the completion of this work. 89-97% R1 = H, Br Conflict of interest R2 = alkyl, aryl Scheme 5 The author declares no conflict of interest. Using the iodocyclization methodology (Scheme 6).17,18 He et al.19 References designed and synthesized a 45-compound library of multi-substituted 1. Khanam H, Shamsuzzaman. Bioactive Benzofuran Derivatives: A Re- benzofurans, and using a high-throughput, cell-based HCV luciferase view. Eur J Med Chem. 2015;97:483–504. reporter assay studied its anti-hepatitis C virus (HCV) activity.19 The optimization of the scaffold resulted in the identification of several 2. Siddoway LA. Amiodarone: Guidelines for Use and Monitoring. Am Fam Physician. 2003;68(11):2189–2196. potent inhibitors (EC50<100nM) of HCV with low cytotoxicity (CC50>25μM), and good selectivity (selectivity index=CC50/EC50, 3. Narimatsu S, Takemi C, Kuramoto S, et al. Stereoselectivity in the Oxi- >371-fold). dation of Bufuralol, a Chiral Substrate, by Human Cytochrome P450s. Chirality. 2003;15(4):333–339. Jung et al.20 recently reported an efficient synthetic approach to polysubstituted benzofurans where 2-methoxyquinone was used as 4. Abu–Hashem AA, Hussein HAR, Aly AS, et al. Synthesis of Benzofuran a benzofuran backbone. The starting quinols were reduced to the Derivatives via Different Methods. Synth Commun. 2014;44(16):2285– phenols, the -OH group was protected and these substrates were further 2312. subjected to iodocyclization conditions affording the corresponding 5. Wu XF, Li Y. Transition Metal–Catalyzed Benzofuran Synthesis. Ne- benzofurans (Scheme 7).20 therlands: Elsevier; 2017. p. 1–71. Raminelli et al.21 recently reported an interesting methodology 6. Godoi B, Schumacher RF, Zeni G. Synthesis of Heterocycles via Elec- for synthesizing diiodo-functionalized benzo[b]furans.21 The reaction trophilic Cyclization of Alkynes Containing Heteroatom. Chem Rev. 2011;111(4):2937–2980. Citation: Mehta S. Benzofuran synthesis through iodocyclization reactions: recent advances. MOJ Biorg Org Chem. 2017;1(7):262‒264. DOI: 10.15406/mojboc.2017.01.00045 Copyright: Benzofuran synthesis through iodocyclization reactions: recent advances ©2017 Mehta 264 7. Gabriele B, Mancuso R, Larock RC. Recent Advances in the Synthe- 15. Danilkina NA, Kulyashova AE, Khlebnikov AF, et al. Electrophilic Cy- sis of Iodoheterocycles via Iodocyclization of Functionalized Alkynes. clization of Aryldiacetylenes in the Synthesis of Functionalized Enediy- Curr Org Chem. 2014;18(3):341–358. nes Fused to a Heterocyclic Core. J Org Chem. 2014;79(19):9018–9045. 8. Mehta S, Waldo JP, Larock RC. Competition Studies in Alkyne Elec- 16. Li YL, Li J, Yu SN, et al. A Concise Approach for the Synthesis of 3–Io- trophilic Cyclization Reactions. J Org Chem. 2009;74(3):1141–1147. doindoles and 3–Iodobenzo[b]furans via Ph3P–Catalyzed Iodocycliza- tion. Tetrahedron. 2015;71(43):8271–8277. 9. Mehta S, Waldo JP, Neuenswander B, et al. Solution–Phase Parallel Synthesis of a Multisubstituted Cyclic Imidate Library. ACS Comb Sci. 17. Yue D, Yao T, Larock RC. Synthesis of 2,3–Disubstituted Benzo[b] 2013;15(5):247–254. furans by the Palladium–Catalyzed Coupling of O–Iodoanisoles and Terminal Alkynes, Followed by Electrophilic Cyclization. J Org Chem. 10. Huang Q, Rui EY, Cobbs M, et. al. Design, Synthesis, and Evaluation of 2005;70(25):10292–10296. NO–Donor Containing Carbonic Anhydrase Inhibitors to Lower Intrao- cular Pressure. J Med Chem. 2015;58(6):2821–2833. 18.
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