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Synthesis 2014; 46(24): 3331-3340
DOI: 10.1055/s-0034-1379141
DOI: 10.1055/s-0034-1379141
paper
A New Route to Pyranocoumarins and Their Benzannulated Derivatives
Weitere Informationen
Publikationsverlauf
Received: 29. Juni 2014
Accepted after revision: 20. August 2014
Publikationsdatum:
15. September 2014 (online)
![](https://www.thieme-connect.de/media/synthesis/201424/lookinside/thumbnails/10.1055-s-0034-1379141-1.jpg)
Abstract
A new protocol based on sequential applications of three atom-economic processes viz. Claisen rearrangement, olefin isomerisation, and ring-closing diene metathesis has been developed to access a range of linear and angularly fused pyranocoumarin derivatives. Incorporation of enyne (in place of diene) metathesis and Diels–Alder reaction in the sequence has allowed the corresponding benzannulated derivatives to be prepared in good yields.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
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References
- 1 Ellis GP, Lockhart IM. The Chemistry of Heterocyclic Compounds: Chromenes, Chromanones, and Chromones . Vol. 31. Wiley-VCH; New York: 2007: 1196
- 2 Cai Y, Bennett D, Nair RV, Ceska O, Ashwood-Smith MJ, DiGiovannil J. Chem. Res. Toxicol. 1993; 6: 872
- 3 Mali RS, Joshi PP, Sandhu PK, Manekar-Tilve A. J. Chem. Soc., Perkin Trans. 1 2002; 1: 371 ; and references cited therein
- 4 Kulkarni MV, Kulkarni GM, Lin CH, Sun CM. Curr. Med. Chem. 2006; 13: 2795
- 5 Xie L, Takeuchi Y, Cosentino LM, McPhail AT, Lee KH. J. Med. Chem. 2001; 44: 664
- 6 Trost BM, Toste FD, Greenman K. J. Am. Chem. Soc. 2003; 125: 4518
- 7a Nicolaou KC, Pfefferkorn JA, Roecker AJ, Cao G.-Q, Barluenga S, Mitchell HJ. J. Am. Chem. Soc. 2000; 122: 9939
- 7b Nicolaou KC, Pfefferkorn JA, Cao G.-Q. Angew. Chem. Int. Ed. 2000; 39: 734
- 8 Liu Y, Zhu J, Qian J, Jiang B, Xu Z. J. Org. Chem. 2011; 76: 9096
- 9 Yadav JS, Reddy BV. S, Naveenkumar V, Srinivasa Rao R, Nagaiah K. Synthesis 2004; 1783
- 10 Karami B, Khodabakshi S, Eskandari K. Tetrahedron Lett. 2012; 53: 1445
- 11a Selles P, Mueller U. Org. Lett. 2004; 6: 277
- 11b Kotali A, Lafazanis IS, Harris PA. Synthesis 2009; 836
- 11c Ahadi S, Zolghadr M, Khavasi HR, Bazgir A. Org. Biomol. Chem. 2013; 11: 279
- 11d Farag NA. H, El-tayeb W. Eur. J. Med. Chem. 2010; 45: 317
- 11e Khatri AI, Samant SD. Tetrahedron Lett. 2014; 55: 2362
- 12 Huang CN, Kuo PY, Lin CH, Yang DY. Tetrahedron 2007; 63: 10025
- 13a Jaggavarapu SR, Kamalakaran AS, Nanubolu JB, Jalli VP, Gangisetty SK, Gaddamanugu G. Tetrahedron Lett. 2014; 55: 3670
- 13b Bagdi AK, Majee A, Hajra A. Tetrahedron Lett. 2013; 54: 3892
- 13c Ma W, Wang X, Yan F, Wu L, Wang Y. Monatsh. Chem. 2011; 142: 163
- 13d Kidwai M, Poddara R, Diwaniyan S, Kuhad RC. Synth. Commun. 2011; 41: 695
- 14a Chattopadhyay SK, Maity S, Panja S. Tetrahedron Lett. 2002; 43: 7781
- 14b Chattopadhyay SK, Dey R, Biswas S. Synthesis 2005; 403
- 14c Chattopadhyay SK, Pal BK, Maity S. Chem. Lett. 2003; 32: 1190
- 14d Chattopadhyay SK, Biswas T, Maity S. Synlett 2006; 2211
- 15a Rotzoll S, Gorls H, Langer P. Synthesis 2008; 45
- 15b Pain C, Celanire S, Guillaumet G, Joseph B. Synlett 2003; 2089
- 15c Litinas KE, Mangos A, Nikkou TE, Hadjipavlou-Litina DJ. J. Enzyme Inhib. Med. Chem. 2011; 26: 805
- 15d Majumdar KC, Rahaman H, Muhuri S, Roy B. Synlett 2006; 466
- 15e Kotha S, Mandal K. Tetrahedron Lett. 2004; 45: 1391
- 16 Kaufman KD. J. Org. Chem. 1961; 26: 117
- 17a Wakamatsu H, Nishida M, Adachi N, Mori M. J. Org. Chem. 2000; 65: 3966
- 17b van Otterlo WA. L, Ngidi EL, de Koning CB. Tetrahedron Lett. 2003; 44: 6483
- 17c van Otterlo WA. L, Pathak R, de Koning CB. Synlett 2003; 1859
- 17d van Otterlo WA. L, Morgans GL, Khanye SD, Aderibigbe BA. A, Michael JP, Billing DG. Tetrahedron Lett. 2004; 45: 9171
- 18a van Otterlo WA. L, de Koning CB. Chem. Rev. 2009; 109: 3743
- 18b Schmidt B. Eur. J. Org. Chem. 2004; 1865
- 18c Dragutan V, Dragutan I. J. Organomet. Chem. 2006; 691: 5129
- 18d Donohoe TJ, O’Riordan TJ. C, Rosa CP. Angew. Chem. Int. Ed. 2009; 48: 1014
- 18e Taher A, Aderibigbe BA, Morgans GL, Madeley LG, Khanye SD, van der Westhuizen L, Fernandes MA, Smith VJ, Michael JP, Green IR, van Otterlo WA. L. Tetrahedron 2013; 69: 2038
- 18f Yadav DB, Morgans GL, Aderibigbe BA, Madeley LG, Fernandes MA, Michael JP, de Koning CB, van Otterlo WA. L. Tetrahedron 2011; 67: 2991
- 18g Kashaya Y, Hoshi K, Terada Y, Nishida A, Shuto S, Arisawa M. Eur. J. Org. Chem. 2009; 4606
- 18h Gross U, Nieger M, Brase S. Org. Lett. 2009; 11: 4740
- 18i Chattopadhyay SK, Ghosh D, Mondal P, Ghosh SK. Synthesis 2012; 44: 2448
- 18j Bennasar ML, Roca T, Monneris M, Garcia-Diaz D. J. Org. Chem. 2006; 71: 7028
- 19a Kirsch SF, Zhu Z.-B. Chem. Commun. 2013; 49: 2272
- 19b Fischmeister C, Bruneau C. Beilstein J. Org. Chem. 2011; 7: 156
- 19c Li J, Lee D. Eur. J. Org. Chem. 2011; 4269
-
19d Monfette S, Fogg SD. Chem. Rev. 2009; 109: 3783
- 19e Herndou JW. Coord. Chem. Rev. 2009; 253: 86
-
19f Villar H, Frings M, Bolm C. Chem. Soc. Rev. 2007; 36: 55
- 19g Chattopadhyay SK, Karmakar S, Biswas T, Majumdar KC, Rahman H, Roy B. Tetrahedron 2007; 63: 3919
-
19h Diver ST, Giessert AJ. Chem. Rev. 2004; 104: 1317
- 19i Diver ST. J. Mol. Catal. A: Chem. 2006; 254: 29
- 19j Kaliappan KP. Lett. Org. Chem. 2005; 678
- 19k Poulsen CS, Madsen R. Synthesis 2003; 1
- 19l Sémeril D, Bruneau C, Dixneuf PH. Adv. Synth. Catal. 2002; 344: 585
- 19m Mori M. Top. Organomet. Chem. 1999; 1: 133
- 19n Benedetti E, Lomazzi M, Tibiletti F, Goddard J.-P, Fensterbank L, Malacria M, Palmisano G, Penoni A. Synthesis 2012; 44: 3523
-
20a Yoshida K, Nishii K, Kano Y, Wada S, Yanagisawa A. J. Org. Chem. 2014; 79: 4231
- 20b Moodie LW. K, Larsen DS. Eur. J. Org. Chem. 2014; 1684
- 20c Hill-Cousins JT, Salim SS, Bakar YM, Bellingham RD, Light ME, Brown RC. D. Tetrahedron 2014; 70: 3700
- 20d Mailyan AK, Krylov IM, Bruneau C, Dixneuf PH, Osipov SN. Eur. J. Org. Chem. 2013; 5353
- 20e Fustero S, Bello P, Miro J, Sánchez-Roselló M, Haufe G, del Pozo C. Beilstein J. Org. Chem. 2013; 9: 2688
-
20f Betkekar VV, Panda S, Kaliappan KP. Org. Lett. 2012; 14: 198
- 20g Subrahmanyam AV, Palanichamy K, Kaliappan KP. Chem. Eur. J. 2010; 16: 8545
- 20h Kotha S, Meshram M, Tiwari A. Chem. Soc. Rev. 2009; 38: 2065
- 20i Rosillo M, Domínguez G, Casarubios L, Amador U, Pérez-Castells J. J. Org. Chem. 2004; 69: 2084
- 21a Chattopadhyay SK, Biswas T, Neogi K. Chem. Lett. 2006; 35: 376
- 21b Chattopadhyay SK, Roy SP, Ghosh D, Biswas G. Tetrahedron Lett. 2006; 47: 6895
- 21c Biswas T, Biswas T, Chattopadhyay SK. Tetrahedron: Asymmetry 2010; 21: 232
- 21d Mondal P, Thunder L, Chattopadhyay SK. Tetrahedron Lett. 2012; 53: 1328
- 21e Chattopadhyay SK, Ghosh D, Neogi K. Synth. Commun. 2007; 37: 1535
- 22a Kotha S, Mandal K, Tiwari A, Mobin SM. Chem. Eur. J. 2006; 12: 8024
- 22b Majumdar KC, Maji PK, Rahaman H, Roy B. Lett. Org. Chem. 2006; 3: 845
-
22c Takahashi H, Yoshida K, Yanagisawa A. J. Org. Chem. 2009; 74: 3632
- 22d Ben-Othman R, Othman M, Coste S, Decroix B. Tetrahedron 2008; 64: 559
- 22e Virolleaud M, Piva O. Eur. J. Org. Chem. 2007; 1606
- 22f Kummer DA, Brenneman JB, Martin SF. Org. Lett. 2005; 7: 4621
- 22g Imhof S, Blechert S. Synlett 2003; 609
- 22h Banti D, North M. Tetrahedron Lett. 2002; 43: 1561
- 22i Moreno-Mañas M, Pleixats R, Santamaria A. Synlett 2001; 1784
- 22j Duboc R, Henaut C, Savignac M, Genet JP, Bhatnagar N. Tetrahedron Lett. 2001; 42: 2461
- 22k Bentz D, Laschat S. Synthesis 2000; 1766
- 22l Lane C, Snieckus V. Synlett 2000; 1294
- 22m Schürer SC, Blechert S. Chem. Commun. 1999; 1203
- 22n Saito N, Sato Y, Mori M. Org. Lett. 2002; 4: 803
-
23a Hansen EC, Lee D. Acc. Chem. Res. 2006; 39: 509
- 23b Boyer FD, Hanna I. Eur. J. Org. Chem. 2006; 471
-
23c Lloyd-Jones GC, Margue RG, Vries JG. Angew. Chem. Int. Ed. 2005; 44: 7442
- 23d Kitamura T, Sato Y, Mori M. Adv. Synth. Catal. 2002; 344
- 23e Furstner A, Ackermann L, Gabor B, Goddard R, Lehmann CW, Mynott R, Stelzer F, Thiel OR. Chem. Eur. J. 2001; 7: 3236
- 23f Randl S, Lucas N, Connon SJ, Blechert S. Adv. Synth. Catal. 2002; 344: 631
- 24 Lee H.-Y, Kim HY, Tae H, Kim BG, Lee J. Org. Lett. 2003; 5: 3439
- 25 For a recent study, see: Solans-Monfort X. Dalton Trans. 2014; 4573
- 26a Yamamoto Y, Matsui K, Shibuya M. Org. Lett. 2014; 16: 1806
- 26b Matos MJ, Janeiro P, Santana L, Uriarte E, Oliveira-Brett AM. J. Electroanal. Chem. 2014; 726: 62
- 26c Borah P, Naidu PS, Majumder S, Bhuyan PJ. RSC Advances 2013; 3: 20450
- 26d Al-Kawkabani A, Boutemeur-Kheddis B, Makhloufi-Chebli M, Hamdi M, Talhi O, Silva AM. S. Tetrahedron Lett. 2013; 54: 5111
- 26e Gohain M, Van Tonder JH, Bezuidenhoudt BC. B. Tetrahedron Lett. 2013; 54: 3773
- 26f Majumdar KC, Chattopadhyay B. Synth. Commun. 2006; 36: 3125
- 27 Rangaswami S, Seshadri TR. Proc. Indian Acad. Sci., Sect. A 1938; 7: 8
- 28 Guiotto A, Manzini P, Chilin A, Pastorini G, Rodighiero P. J. Heterocycl. Chem. 1985; 22: 649
- 29 Rodighiero P, Manzini P, Pastorini G, Chilin A, Guitto A. J. Heterocycl. Chem. 1987; 24: 485
- 30 Majumdar KC, Chatterjee P. J. Chem. Res. 1996; 462
For some recent assorted reports, see:
For some recent reviews on isomerisation–RCM sequences, see:
For some recent reports, see:
For some reviews on RCEYM and related issues, see:
For some recent reports, see: