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Synthesis 2016; 48(21): 3803-3811
DOI: 10.1055/s-0035-1561653
DOI: 10.1055/s-0035-1561653
paper
Synthesis of Activated Cyclopropanes by MHIRC Strategy: A Facile and Efficient Approach to Spirocyclopropanes Using N-Halosulfonamides
Further Information
Publication History
Received: 17 February 2016
Accepted after revision: 28 April 2016
Publication Date:
20 June 2016 (online)
Abstract
In this study, a one-pot, three-component reaction of two molecules of indane-1,3-dione with aromatic aldehydes for the synthesis of spirocyclopropylindanediones using poly(N-bromo-N-ethylbenzene-1,3-disulfonamide) (PBBS), N,N,N′,N′-tetrabromobenzene-1,3-disulfonamide (TBBDA), poly(N-chloro-N-ethylbenzene-1,3-disulfonamide) (PCBS), and N,N,N′,N′-tetrachlorobenzene-1,3-disulfonamide (TCBDA) as novel reagents has been developed. In addition, an effective and simple domino procedure for the preparation of spirodicyanocyclopropylindanediones from indane-1,3-dione and 2-arylidenemalononitriles is reported. These reactions involve Michael addition, halogenation, and intramolecular ring-closing (MHIRC) reaction sequences.
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References
- 1a Donaldson WA. Tetrahedron 2001; 57: 8589
- 1b Schneider TF, Kaschel J, Werz DB. Angew. Chem. Int. Ed. 2014; 53: 2
- 2a Wong HN. C, Hon M.-Y, Tse C.-W, Yip Y.-C, Tanko J, Hudlicky T. Chem. Rev. 1989; 89: 165
- 2b Ajay Kumar K. Int. J. Pharm. Pharm. Sci. 2013; 5: 467
-
3 Maas G. Chem. Soc. Rev. 2004; 33: 183
- 4a King SB, Stratford ES, Craig CR, Fifer EK. Pharm. Res. 1995; 12: 1240
- 4b Fraser W, Suckling CJ, Wood HC. S. J. Chem. Soc., Perkin Trans. 1 1990; 3137
- 4c Kim S.-H, Pudzianowski AT, Leavitt KJ, Barbosa J, McDonnell PA, Metzler WJ, Rankin BM, Liu R, Vaccaro W, Pitts W. Bioorg. Med. Chem. Lett. 2005; 15: 1101
- 5 Lebel H, Marcoux JF, Molinaro C, Charette AB. Chem. Rev. 2003; 103: 977
- 6a Davies HM. L, Panaro SA. Tetrahedron Lett. 1999; 40: 5287
- 6b Bauta W, Dodd J, Bullington J, Gauthier D, Leo G, McDonnell P. Tetrahedron Lett. 2000; 41: 1491
- 6c Muthusamy S, Gunanathan C. Synlett 2003; 1599
- 6d Rasool N, Rashid MA, Adeel M, Gorls H, Langer P. Tetrahedron Lett. 2008; 49: 2254
- 6e Pirrung MC, Liu H. Org. Lett. 2003; 5: 1983
- 6f Revuelta J, Cicchi S, Faggi C, Kozhushkov SI, de Meijere A, Brandi A. J. Org. Chem. 2006; 71: 2417
- 6g Kuethe JT, Zhao D, Humphrey GR, Journet M, McKeown AE. J. Org. Chem. 2006; 71: 2192
- 7a Krysiak J, Kato T, Gornitzka H, Baceiredo A, Mikolajczyk M, Bertrand G. J. Org. Chem. 2001; 66: 8240
- 7b Singh VK, DattaGupta A, Sekar G. Synthesis 1997; 137
- 7c Grieco PA, Finkelhor RS. Tetrahedron Lett. 1972; 13: 3781
- 7d Trost BM. J. Am. Chem. Soc. 1967; 89: 138
- 7e Yamamote Y, Schmibaur H. J. Chem. Soc., Chem. Commun. 1975; 668
- 7f Muller P, Allenbach Y, Robert E. Tetrahedron: Asymmetry 2003; 14: 779
- 8a Luo J, Wu B, Chen M.-W, Jiang G.-F, Zhou Y.-G. Org. Lett. 2014; 16: 2578
- 8b Scribner RM, Sausen GN, Prichard WW. J. Org. Chem. 1960; 25: 1440
- 8c Liu X.-G, Wei Y, Shi M. Tetrahedron 2010; 66: 304
- 9a Liao W.-W, Li K, Tang Y. J. Am. Chem. Soc. 2003; 125: 13030
- 9b Maghsoodlou MT, Khorassani SM. H, Heydari R, Charati FR, Hazeri N, Lashkari M, Rostamizadeh M, Marandi G, Sobolev A, Makha M. Tetrahedron Lett. 2009; 50: 4439
-
10 Ma S, Jiao N, Yang Q, Zheng Z. J. Org. Chem. 2004; 69: 6463
- 11 Okamoto N, Sasaki M, Kawahata M, Yamaguchi K, Takeda K. Org. Lett. 2006; 8: 1889
- 12 Li J, Liao S.-H, Xiong H, Zhou Y.-Y, Sun X.-L, Zhang Y, Zhou X.-G, Tang Y. Angew. Chem. Int. Ed. 2012; 51: 8838
- 13 Little RD, Dawson JR. Tetrahedron Lett. 1980; 21: 2609
- 14 Stereoselective Multiple Bond-Forming Transformations in Organic Synthesis. Rodriguez J, Bonne D. Wiley; Hoboken: 2015
- 15 Piras L, Moccia M, Cortigiani M, Adamo MF. A. Catalysts 2015; 5: 595
- 16 Xin X, Zhang Q, Liang Y, Zhanga R, Dong D. Org. Biomol. Chem. 2014; 12: 2427
- 17 Dorofeeva EO, Elinson MN, Vereshchagin AN, Stepanov NO, Bushmarinov IS, Belyakov PA, Sokolova OO, Nikishin GI. RSC Adv. 2012; 2: 4444
- 18 Vereshchagin AN, Elinson MN, Dorofeeva EO, Zaimovskaya TA, Stepanov NO, Gorbunov SV, Belyakov PA, Nikishin GI. Tetrahedron 2012; 68: 1189
- 19 Elinson MN, Vereshchagin AN, Stepanov NO, Belyakov PA, Nikishin GI. Tetrahedron Lett. 2010; 51: 6598
- 20 Elinson MN, Merkulova VM, Ilovaisky AI, Nikishin GI. J. Heterocycl. Chem. 2013; 50: 1236
- 21 Elinson MN, Dorofeeva EO, Vereshchagin AN, Nasybullin RF, Egorov MP. Catal. Sci. Technol. 2015; 5: 2384
- 22 Vereshchagin AN, Elinson MN, Dorofeeva EO, Stepanov NO, Zaimovskaya TA, Nikishin GI. Tetrahedron 2013; 69: 1945
- 23 Elinson MN, Vereshchagin AN, Stepanov NO, Zaimovskaya TA, Merkulova VM, Nikishin GI. Tetrahedron Lett. 2010; 51: 428
- 24 Vereshchagin AN, Elinson MN, Stepanov NO, Nikishin GI. Mendeleev Commun. 2009; 19: 324
- 25 Elinson MN, Feducovich SK, Stepanov NO, Vereshchagin AN, Nikishin GI. Tetrahedron 2008; 64: 708
- 26 Wang G.-W, Gao J. Org. Lett. 2009; 11: 2385
- 27 Russo A, Meninno S, Tedesco C, Lattanzi A. Eur. J. Org. Chem. 2011; 5096
- 28 Shchepin VV, Stepanyan YG, Silaichev PS. Russ. J. Gen. Chem. 2008; 78: 929
- 29 Veisi H, Ghorbani-Vaghei R. Tetrahedron 2010; 66: 7445
- 30 Koval IV. Russ. J. Org. Chem. 2002; 38: 301
- 31 Umemoto T, Fukami S, Tomizawa G, Harasawa K, Kawada K, Tomita K. J. Am. Chem. Soc. 1990; 112: 8563
- 32 Kolvari E, Ghorbani-Choghamarani A, Salehi P, Shirini F, Zolfigol MA. J. Iran. Chem. Soc. 2007; 4: 126
- 33a Ghorbani-Vaghei R, Jalili H. Synthesis 2005; 1099
- 33b Ghorbani-Vaghei R, Shahbazi H, Veisi H. Tetrahedron Lett. 2012; 53: 2325
- 34 Ghorbani-Vaghei R, Maghbooli Y, Mahmoodi J, Shahriari A. RSC Adv. 2015; 5: 74336
- 35 Ghorbani-Vaghei R, Salimi Z, Malaekehpoor SM, Eslami F, Noori S. RSC Adv. 2014; 4: 33582
- 36 Ghorbani-Vaghei R, Shahriari A, Salimi Z, Hajinazari S. RSC Adv. 2015; 5: 3665
- 37 Ghorbani-Vaghei R, Amiri M, Karimi-Nami R, Salimi Z. RSC Adv. 2013; 3: 25924
- 38 Ghorbani-Vaghei R, Chegini M, Veisi H, Karimi-Tabar M. Tetrahedron Lett. 2009; 50: 1861
- 39 Ghorbani-Vaghei R, Karimi-Nami R, Toghraei-Semiromi Z, Amiri M, Salimi Z, Ghavidel M. C. R. Chim. 2014; 17: 324
- 40 Supuran CT, Scozzafava A. J. Enzyme Inhib. 2000; 15: 597
- 41a Ogiwara Y, Takahashi K, Kitazawa T, Sakai N. J. Org. Chem. 2015; 80: 3101
- 41b Wada S, Suzuki H. Tetrahedron Lett. 2003; 44: 399
- 41c Kaupp G, Naimi-Jamal MR, Schmeyers J. Tetrahedron 2003; 59: 3753
- 41d Barge M, Salunkhe R. RSC Adv. 2014; 4: 31177
- 41e Wu D, Ren Z, Cao W, Tong W. Synth. Commun. 2005; 35: 3157