Synthesis 2015; 47(14): 1961-1989
DOI: 10.1055/s-0034-1378705
review
© Georg Thieme Verlag Stuttgart · New York

Recent Advances in Iodine Monochloride Mediated Electrophilic Cyclizations

Sarbjit Singh
U.G.C. Sponsored Centre for Advance Studies in Chemistry, Department of Chemistry, Guru Nanak Dev University, Amritsar, 143005, India   Email: sschimni@yahoo.com
,
Swapandeep Singh Chimni*
U.G.C. Sponsored Centre for Advance Studies in Chemistry, Department of Chemistry, Guru Nanak Dev University, Amritsar, 143005, India   Email: sschimni@yahoo.com
› Author Affiliations
Further Information

Publication History

Received: 01 February 2015

Accepted after revision: 02 March 2015

Publication Date:
24 June 2015 (online)


Abstract

Recent progress in electrophilic cyclizations has led to the development of many electrophilic cyclizing agents. Among them, iodine monochloride (ICl) has recently emerged as one of the most promising. In this Review, we highlight the advances in iodine monochloride mediated electrophilic cyclizations from 2000 to 2014. In addition, the different transformations of organoiodine compounds (the usual products of these electrophilic cyclizations) are discussed.

1 Introduction

2 Iodine Monochloride Mediated Electrophilic Cyclizations

2.1 Synthesis of Quinoline and Isoquinoline Derivatives

2.2 Synthesis of Isocoumarins and α-Pyrone Derivatives

2.3 Synthesis of Furan Derivatives

2.4 Synthesis of Isoxazoles

2.5 Synthesis of Selenium-Containing Compounds

2.6 Synthesis of Phosphorus-Containing Compounds

2.7 Synthesis of Spiro Compounds

2.8 Synthesis of Polysubstituted Aromatic Compounds

2.9 Miscellaneous

3 Summary and Outlook

 
  • References

    • 1a Baldwin JE. J. Chem. Soc., Chem. Commun. 1976; 734
    • 1b Baldwin JE, Cutting J, Dupont W, Kruse L, Silberman L, Thomas RC. J. Chem. Soc., Chem. Commun. 1976; 736
  • 2 Borrelli F, Campagnuolo C, Capasso R, Fattorusso E, Taglialatela-Scafati O. Eur. J. Org. Chem. 2004; 3227
  • 3 Zito, K. Methyl iodide gains state OK for use on crops. San Francisco Chronicle, Dec 2, 2010. http://www.sfgate.com/green/article/Methyl-iodide-gains-state-OK-for-use-on-crops-2455128.php.
    • 4a Russo A, De Fusco C, Lattanzi A. RSC Adv. 2012; 2: 385
    • 4b Veitch GE, Jacobsen EN. Angew. Chem. Int. Ed. 2010; 49: 7332
    • 4c Baughman TW, Sworen JC, Wagener KB. Tetrahedron 2004; 60: 10943
    • 4d Hachiya I, Shimizu M. Tetrahedron Lett. 2014; 55: 2781
    • 4e Kirschning A, Yusubov MS, Yusubova RY, Chi K.-W, Park JY. Beilstein J. Org. Chem. 2007; 3: No. 19
    • 4f Reddy Marri M, Macharla AK, Peraka S, Nama N. Tetrahedron Lett. 2011; 52: 6554
    • 4g Koposov AY, Boyarskikh VV, Zhdankin VV. Org. Lett. 2004; 6: 3613
    • 4h Zhao J, Zhang Q, Liu L, He Y, Li J, Li J, Zhu Q. Org. Lett. 2012; 14: 5362
    • 5a Banerjee AK, Manuel SL, Elvia VC. Curr. Org. Chem. 2011; 15: 1058
    • 5b Godoi B, Schumacher RF, Zeni G. Chem. Rev. 2011; 111: 2937
    • 6a Gryzło B, Kulig K. Mini Rev. Med. Chem. 2014; 14: 332
    • 6b Michael JP. Nat. Prod. Rep. 1997; 14: 605
    • 7a Markees DG, Dewey VC, Kidder GW. J. Med. Chem. 1970; 13: 324
    • 7b Alhaider AA, Abdelkader MA, Lien EJ. J. Med. Chem. 1985; 28: 1394
    • 7c Campbell SF, Hardstone JD, Palmer MJ. J. Med. Chem. 1988; 31: 1031
    • 7d De SK, Gibbs RA. Tetrahedron Lett. 2005; 46: 1647
    • 8a Newhouse BJ, Bordner J, Augeri DJ, Litts CS, Kleinman EF. J. Org. Chem. 1992; 57: 6991
    • 8b Torii S, Xu LH, Sadakane M, Okumoto H. Synlett 1992; 513
    • 8c Miyachi N, Yanagawa Y, Iwasaki H, Ohara Y, Hiyama T. Tetrahedron Lett. 1993; 34: 8267
    • 8d Croisey-Delcey M, Croisy A, Carrez D, Huel C, Chiaroni A, Ducrot P, Bisagni E, Jin L, Leclercq G. Bioorg. Med. Chem. 2000; 8: 2629
    • 8e Bu X, Deady LW, Denny WA. Aust. J. Chem. 2000; 53: 143
    • 8f Blackburn TP, Cox B, Guildord AJ, LeCount DJ, Middlemiss DN, Pearce RJ, Thornber CW. J. Med. Chem. 1987; 30: 2252
    • 8g Amii H, Kishikawa Y, Uneyama K. Org. Lett. 2001; 3: 1109
  • 9 Zhang X, Yao T, Campo MA, Larock RC. Tetrahedron 2010; 66: 1177
  • 10 Huo Z, Gridnev ID, Yamamoto Y. J. Org. Chem. 2010; 75: 1266
  • 11 Ohnmatch CJ, Patel AR, Lutz RE. J. Med. Chem. 1971; 14: 926
  • 12 Sakashita H, Yoshida T, Kitajima H, Takeuchi M, Tanaka Y, Yoshimura T, Akahoshi F, Hayashi Y. WO 2003024942, 2003
  • 13 Dade J, Provot O, Moskowitz H, Mayrargue J, Prina E. Chem. Pharm. Bull. 2001; 49: 480
  • 14 Likhar PR, Subhas MS, Roy S, Kantam ML, Sridhar B, Seth RK, Biswas S. Org. Biomol. Chem. 2009; 7: 85
  • 15 Huang Q, Hunter JA, Larock RC. J. Org. Chem. 2002; 67: 3437
  • 16 Ding Q, Chen Z, Yu X, Peng Y, Wu J. Tetrahedron Lett. 2009; 50: 340
    • 17a Pal S, Chatare V, Pal M. Curr. Org. Chem. 2011; 15: 782
    • 17b Mali RS, Babu KN. J. Org. Chem. 1998; 63: 2488
    • 18a Kvita V, Fischer W. Chimia 1992; 46: 457
    • 18b Posner GH, Nelson TD, Kinter CM, Johnson N. J. Org. Chem. 1992; 57: 4083
  • 19 Yao T, Larock RC. Tetrahedron Lett. 2002; 43: 7401
  • 20 Yao T, Larock RC. J. Org. Chem. 2003; 68: 5936
  • 21 Zhou C, Dubrovsky AV, Larock RC. J. Org. Chem. 2006; 71: 1626
    • 22a Wen S.-S, Wang J, Luo Y.-M, Yang H. Tetrahedron 2014; 70: 9314
    • 22b Liu Z, Zhang X, Larock RC. J. Am. Chem. Soc. 2005; 127: 15716
    • 22c Pal M, Subramanian V, Parasuraman K, Yeleswarapu KR. Tetrahedron 2003; 59: 9563
    • 22d Larock RC, Tian Q. J. Org. Chem. 1998; 63: 2002
    • 22e Pal M, Dakarapu R, Parasuraman K, Subramanian V, Yeleswarapu KR. J. Org. Chem. 2005; 70: 7179
    • 23a Wu ES. C, Cole TE, Davidson TA, Dailey MA, Doring KG, Fedorchuk M, Loch III JT, Thomas TL, Blosser JC, Borrelli AR, Kinsolving CR, Parker RB. J. Med. Chem. 1989; 32: 183
    • 23b Wu ES. C, Loch III JT, Toder BH, Borrelli AR, Gawlak D, Radov LA, Gensmante NP. J. Med. Chem. 1992; 35: 3519
  • 24 Yue D, Ca ND, Larock RC. J. Org. Chem. 2006; 71: 3381
    • 25a Lipshutz BH. Chem. Rev. 1986; 86: 795
    • 25b Dean FM. Advances in Heterocyclic Chemistry . Katritzky AR. Academic Press; New York: 1983
  • 26 Arimitsu S, Jacobsen JM, Hammond GB. J. Org. Chem. 2008; 73: 2886
  • 27 Thongsornkleeb C, Rabten W, Bunrit A, Tummatorn J, Ruchirawat S. Tetrahedron Lett. 2012; 53: 6615
    • 28a Kirilmis C, Ahmedzade M, Servi S, Koca M, Kizirgil A, Kazaz C. Eur. J. Med. Chem. 2008; 43: 300
    • 28b Schultz DM, Prescher JA, Kidd S, Marona-Lewicka D, Nichols DE, Monte A. Bioorg. Med. Chem. 2008; 16: 6242
    • 28c Dixit M, Tripathi BK, Tamrakar AK, Srivastava AK, Kumar B, Goel A. Bioorg. Med. Chem. 2007; 15: 727
  • 29 Manarin F, Roehrs JA, Gay RM, Brandao R, Menezes PH, Nogueira CW, Zeni G. J. Org. Chem. 2009; 74: 2153
  • 30 Kumar KA, Jayaroopa P. Int. J. Pharm. Bio. Sci. 2013; 3: 294
  • 31 Daidone G, Raffa D, Maggio B, Plescia F, Cutuli VM. C, Mangano NG, Caruso A. Arch. Pharm. Pharm. Med. Chem. 1999; 332: 50
  • 32 Tomita K, Takahi Y, Ishizuka R, Kamamura S, Nakagawa M, Ando M, Nakanishi T, Nakamura T, Udaira H. Ann. Sankyo Res. Lab. 1973; 1: 25
  • 33 Giovannoni MP, Vergelli C, Ghelardini C, Galeotti N, Bartolini A, Kal Piaz V. J. Med. Chem. 2003; 46: 1055
  • 34 Li W.-T, Hwang D.-R, Chen C.-P, Shen C.-W, Huang C.-L, Chen T.-W, Lin C.-H, Chang Y.-L, Chang Y.-Y, Lo Y.-K, Tseng H.-Y, Lin C.-C, Song J.-S, Chen H.-C, Chen S.-J, Wu S.-H, Chen C.-T. J. Med. Chem. 2003; 46: 1706
  • 35 Waldo JP, Larock RC. Org. Lett. 2005; 7: 5203
  • 36 Waldo JP, Larock RC. J. Org. Chem. 2007; 72: 9643
    • 37a Crossley JA, Browne DL. J. Org. Chem. 2010; 75: 5414
    • 37b Kromann H, Sløk FA, Johansen TN, Krogsgaard-Larsen P. Tetrahedron 2001; 57: 2195
  • 38 Sharpless KB, Young MW, Lauer RF. Tetrahedron Lett. 1973; 22: 1979
  • 39 Reich HJ. J. Org. Chem. 1975; 40: 2570
  • 40 Sevrin M, Vanende D, Krief A. Tetrahedron Lett. 1976; 30: 2643
  • 41 Sevrin M, Dumont W, Hevesi LD, Krief A. Tetrahedron Lett. 1976; 30: 2647
    • 42a Seebach D, Beck AK. Angew. Chem., Int. Ed. Engl. 1974; 13: 806
    • 42b Reich HJ, Shah SK. J. Am. Chem. Soc. 1975; 97: 3250
  • 43 Silveira CC, Braga AL, Vieira AS, Zeni G. J. Org. Chem. 2003; 68: 662
  • 44 Kesharwani T, Worlikar SA, Larock RC. J. Org. Chem. 2006; 71: 2307
  • 45 Stein AL, da Rocha J, Menezes PH, Zeni G. Eur. J. Org. Chem. 2010; 705
  • 46 Godoi B, Speranc A, Back DF, Brandao R, Nogueira CW, Zeni G. J. Org. Chem. 2009; 74: 3469
  • 47 Alves D, Luchese C, Nogueira CW, Zeni G. J. Org. Chem. 2007; 72: 6726
    • 48a Peng A.-Y, Ding Y.-X. Org. Lett. 2004; 6: 1119
    • 48b Peng A.-Y, Ding Y.-X. Tetrahedron 2005; 61: 10303
    • 49a Xu Y, Prestwich GD. Org. Lett. 2002; 4: 4021
    • 49b Hum G, Lee J, Taylor SD. Bioorg. Med. Chem. Lett. 2002; 12: 3471
    • 49c Pfund E, Lequeux T, Masson S, Vazeux M. Org. Lett. 2002; 4: 843
    • 49d Okomatsu T, Kato J, Sakuma C, Shibuya S. Synlett 2003; 1407
    • 49e Li XF, Bhandari A, Holmes CP, Szardenings AK. Bioorg. Med. Chem. Lett. 2004; 14: 4301
    • 49f Gautier A, Garipova G, Salcedo C, Balieu S, Piettre SR. Angew. Chem. Int. Ed. 2004; 43: 5963
  • 50 Lin Y, Liu J.-T. Tetrahedron Lett. 2006; 47: 6075
  • 51 Kaur K, Mehta DK, Gupta GK, Das R, Kushwah P, Farooq SA. Inventi Impact: Med. Chem. 2013; 180
  • 52 Li C.-W, Wang C.-I, Liao H.-Y, Chaudhuri R, Liu R.-S. J. Org. Chem. 2007; 72: 9203
  • 53 Yu Q.-F, Zhang Y.-H, Yin Q, Tang B.-X, Tang R.-Y, Zhong P, Li J.-H. J. Org. Chem. 2008; 73: 3658
  • 54 Zhang X, Larock RC. J. Am. Chem. Soc. 2005; 127: 12230
    • 55a Chen Y, Liu X, Lee M, Huang C, Inoyatov I, Chen Z, Perl AC, Hersh WH. Chem. Eur. J. 2013; 19: 9795
    • 55b Chen Y, Huang C, Liu X, Perl E, Chen Z, Namgung J. J. Org. Chem. 2014; 79: 3452
  • 56 Sha C.-K, Lee F.-C, Lin H.-H. Chem. Commun. 2001; 39
  • 57 Lin H.-H, Lin G.-I, Lin Y.-R, Liang C.-F, Chen C.-H, Sha C.-K. Tetrahedron Lett. 2006; 47: 1167
    • 58a Schwoerer M. Phys. Bull. 1994; 50: 52
    • 58b Greenham NC, Moratti SC, Bradley DD. C, Friend RH, Holmes AB. Nature 1993; 365: 628
    • 58c Gruner J, Hamer PJ, Friend RH, Huber HJ, Scherf U, Holmes AB. Adv. Mater. 1994; 6: 748
    • 59a Munn RW, Ironside CN. Principles and Application of Nonlinear Optical Materials . Chapman & Hall; London: 1993
    • 59b Prasad PN, Williams DJ. Introduction to Nonlinear Optical Effects in Molecules and Polymers. Wiley; New York: 1991
    • 60a Swager TM, Marsella MJ. Adv. Mater. 1994; 6: 595
    • 60b Marsella MJ, Carroll PJ, Swager TM. J. Am. Chem. Soc. 1994; 116: 9347
    • 60c Matsue T, Nishizawa M, Sawaguchi T, Uchida I. J. Chem. Soc., Chem. Commun. 1991; 1029
    • 61a Ukita T, Nakamura Y, Kubo A, Yamamoto Y, Takahashi M, Kotera J, Ikeo T. J. Med. Chem. 1999; 42: 1293
    • 61b Padwa A, Chiacchio U, Fairfax DJ, Kassir JM, Litrico A, Semones MA, Xu SL. J. Org. Chem. 1993; 58: 6429
    • 61c Xie X, Kozlowski MC. Org. Lett. 2001; 3: 2661
  • 62 Zhang X, Sarkar S, Larock RC. J. Org. Chem. 2006; 71: 236
  • 63 Wang L.-J, Zhu H.-T, Lu L, Yang F, Liu X.-Y, Liang Y.-M. Org. Lett. 2012; 14: 1990
    • 65a Smet M, Shukla R, Fulop L, Dahaen W. Eur. J. Org. Chem. 1998; 2769
    • 65b Miyawaki K, Kawano T, Ueda I. Tetrahedron Lett. 2000; 41: 1447
  • 66 Schmidt RR. Chem. Phys. Lett. 1988; 151: 369
  • 67 Hseuh H.-H, Hsu M.-Y, Wu T.-L, Liu R.-S. J. Org. Chem. 2009; 74: 8448
  • 68 Ego C, Marsitzky D, Becker S, Zhang J, Grimsdale AC, Mullen K, MacKenzie JD, Silva C, Friend RH. J. Am. Chem. Soc. 2003; 125: 437
  • 69 Schmidt-Mende L, Fechtenkotter A, Mullen K, Moons E, Friend RH, MacKenzie JD. Science 2001; 293: 1119
  • 70 Kelley RF, Shin WS, Rybtchinski B, Sinks LE, Wasielewski MR. J. Am. Chem. Soc. 2007; 129: 3173
    • 71a Schmidt R, Ling MM, Oh JH, Winkler M, Konemann M, Bao Z, Wurthner F. Adv. Mater. 2007; 19: 3692
    • 71b Gsänger M, Oh JH, Könemann M, Höffken HW, Krause A, Bao Z, Würthner F. Angew. Chem. Int. Ed. 2010; 49: 740
  • 72 Li Y, Wang C, Li C, Motta SD, Negri F, Wang Z. Org. Lett. 2012; 14: 5278
  • 73 Zhang Z, Lei T, Yan Q, Pei J, Zhao D. Chem. Commun. 2013; 49: 2882
  • 74 Mo J, Choi W, Min J, Kim C.-E, Eom D, Kim SH, Lee PH. J. Org. Chem. 2013; 78: 11382
  • 75 Morandim AA, Bergamo DC. B, Kato MJ, Cavalheiro AJ, Bolzani VS, Furlan M. Phytochem. Anal. 2005; 16: 282
  • 76 Bonadies F, Di Fabio R, Bonini C. J. Org. Chem. 1984; 49: 1647
    • 77a Zhendong J, Ying K. WO 2004058738, 2004
    • 77b Iwata N, Wang N, Yao X, Kitanaka S. J. Nat. Prod. 2004; 67: 1106
    • 77c Hu H, Harrison TJ, Wilson PD. J. Org. Chem. 2004; 69: 3782
  • 78 Korec R, Sensch KH, Zoukas T. Arzneim. Forsch. 2000; 50: 122
  • 79 Worlikar SA, Kesharwani T, Yao T, Larock RC. J. Org. Chem. 2007; 72: 1347
    • 80a Nishiyama T, Chiba S, Yamada Y. Eur. J. Pharmacol. 2008; 596: 56
    • 80b Taylor EC, Zhou P, Jenning LD, Mao Z, Hu B, Jun J.-G. Tetrahedron Lett. 1997; 38: 521
    • 80c Ferland J.-M, Demerson CA, Humber LG. Can. J. Chem. 1985; 63: 361
    • 80d Lippmann W. U.S. Patent 4267189, 1981 ; Chem. Abstr. 1981, 95, 61988m.
  • 81 Rao T, Larock RC. J. Org. Chem. 2005; 70: 1432
    • 82a Rao YS. Chem. Rev. 1964; 64: 353
    • 82b Rao YS. Chem. Rev. 1976; 76: 625
    • 83a Higuchi Y, Shimoma F, Ando M. J. Nat. Prod. 2003; 66: 810
    • 83b Hislop J.-A, Hunt MB, Fielder S, Rowan DD. J. Agric. Food Chem. 2004; 52: 7075
    • 83c Frediani P, Rosi L, Frediani M, Bartolucci C, Bambagiotti-Alberti M. J. Agric. Food Chem. 2007; 55: 3877
  • 84 Just ZW, Larock RC. J. Org. Chem. 2008; 73: 2662
  • 85 Cui P, Xu L, Shi Z, Gan L. J. Org. Chem. 2011; 76: 4210
  • 86 Brookes PA, Barrett AG. M. J. Org. Chem. 2014; 79: 8706