Synthesis, Inhaltsverzeichnis Synthesis 2018; 50(08): 1667-1674DOI: 10.1055/s-0036-1591758 paper © Georg Thieme Verlag Stuttgart · New YorkConstruction of Functionalized (Dihydro)thieno[2,3-c]chromene Derivatives via a Domino Michael Addition/Intramolecular Cyclization Reaction Autor*innen Institutsangaben Li-Si-Han Yu Department of Chemistry and Life Sciences, Zhejiang Normal University, 321004 Jinhua, P. R. of China eMail: xiejw@zjnu.edu.cn Jian-Lian Dong Department of Chemistry and Life Sciences, Zhejiang Normal University, 321004 Jinhua, P. R. of China eMail: xiejw@zjnu.edu.cn Zhi-Jian Gao Department of Chemistry and Life Sciences, Zhejiang Normal University, 321004 Jinhua, P. R. of China eMail: xiejw@zjnu.edu.cn Jing Wang Department of Chemistry and Life Sciences, Zhejiang Normal University, 321004 Jinhua, P. R. of China eMail: xiejw@zjnu.edu.cn Jian-Wu Xie* Department of Chemistry and Life Sciences, Zhejiang Normal University, 321004 Jinhua, P. R. of China eMail: xiejw@zjnu.edu.cn Artikel empfehlen Abstract Artikel einzeln kaufen(opens in new window) Alle Artikel dieser Rubrik(opens in new window) Abstract A one-pot synthesis of substituted (dihydro)thieno[2,3-c]chromene derivatives was developed through a Lewis base catalyzed domino Michael addition/intramolecular cyclization reaction between 3-nitro-2H-chromenes and thioamides. The desired (dihydro)thieno[2,3-c]chromene derivatives were prepared with a large substrate scope (22 examples) and excellent diastereoselectivity in moderate to excellent yields. Key words Key words3-nitro-2H-chromenes - thioamides - domino reactions - thieno[2,3-c]chromenes - heterocycles Volltext Referenzen References 1a Nicolaou KC. Pfefferkorn JA. Roecker AJ. Cao G.-Q. Barluenga S. Mitchell HJ. J. Am. Chem. Soc. 2000; 122: 9939 1b Nicolaou KC. Pfefferkorn JA. Mitchell HJ. Roecker AJ. Barluenga S. Cao G.-Q. Affleck RL. Lillig JE. J. Am. Chem. Soc. 2000; 122: 9954 1c Nicolaou KC. Pfefferkorn JA. Barluenga S. Mitchell HJ. Roecker AJ. Cao G.-Q. J. Am. Chem. Soc. 2000; 122: 9968 1d Zeni G. Larock RC. Chem. Rev. 2004; 104: 2285 1e Mori J. Iwashima M. Takeuchi M. Saito H. Chem. Pharm. Bull. 2006; 54: 391 1f Kashiwada Y. Yamazaki K. Ikeshiro Y. Yamasisbi T. Fujioka T. Milashi K. Mizuki K. Cosentino LM. Fowke KS. Natschke LM. Lee K.-H. Tetrahedron 2001; 57: 1559 2a Foye WO. In Principi Di Chemico Farmaceutica . Piccin; Padova: 1991: 416 2b Andreani LL. Lapi E. Boll. Chim. Farm. 1960; 99: 583 2c Zhang YL. Chen BZ. Zheng KQ. Xu ML. Lei XH. Yao Xue Bao. 1982; 17: 17 , Chem. Abstr. 1982, 96, 135383e 2d Bonsignore L. Loy G. Secci D. Calignano A. Eur. J. Med. Chem. 1993; 28: 517 2e Witte EC. Neubert P. Roesch A. Ger. Offen DE Cl. C07D405/12, 1986 ; Chem. Abstr. 1986, 104, 224915f 3a Zempleni J. Wijeratne SS. K. Hassan YI. BioFactors 2009; 35: 36 3b Benetti S. De Risi C. Pollini GP. Zanirato V. Chem. Rev. 2012; 112: 2129 4 Chorghade MS. Gurjar MK. Palakodety RK. Lalitha SV. S. Sadalapure K. Adhikari SS. Murugaiah AM. S. Rao BV. Talukdar A. Talukdar A. Islam A. Hariprasad C. Rao AV. R. Patent Application WO 1999-US15050, 1999 ; CAN 132: 93203 5 Haraguchi K. Shimada H. Tanaka H. Hamasaki T. Baba M. Gullen EA. Dutschman GE. Cheng Y.-C. J. Med. Chem. 2005; 51: 1885 6 El-Aasr M. Fujiwara Y. Takeya M. Ono M. Nakano D. Okawa M. Kinjo J. Ikeda T. Miyashita H. Yoshimitsu H. Nohara T. Chem. Pharm. Bull. 2011; 59: 1340 7a Hou X. Majik MS. Kim K. Pyee Y. Lee Y. Alexander V. Chung HJ. Lee HW. Chandra G. Lee JH. Park SG. Choi WJ. Kim HO. Phan K. Gao ZG. Jacobson KA. Choi S. Lee SK. Jeong LS. J. Med. Chem. 2012; 55: 342 8a Booth H. Huckle D. Lockhart IM. J. Chem. Soc., Perkin Trans. 2 1973; 227 8b Rene L. Blanco L. Royer R. Cavier R. Lemoine J. Eur. J. Med. Chem. 1977; 12: 385 8c Rene L. Royer R. Eur. J. Med. Chem.-Chim. Ther. 1982; 17: 89 8d Deshpande SR. Mathur HH. Trivedi GK. Synthesis 1983; 835 8e Ono N. Sugi K. Ogawa T. Aramaki S. J. Chem. Soc., Chem. Commun. 1993; 1781 8f Johansson L. Sohn D. Thorberg S.-O. Jackson DM. Kelder D. Larsson L.-G. Renyi L. Ross SB. Wallsten C. Eriksson H. Hu P.-S. Jerning E. Mohell N. Westlind-Danielsson A. J. Pharmacol. Exp. Ther. 1997; 283: 216 8g Nyerges M. Virányi A. Marth G. Dancsó A. Blaskó G. Töke L. Synlett 2004; 2761 8h Muruganantham R. Mobin SM. Namboothiri IN. N. Org. Lett. 2007; 9: 1125 8i Kolokythas G. Kostakis IK. Pouli N. Marakos P. Kousidou OC. Tzanakakis GN. Karamanos NK. Eur. J. Med. Chem. 2007; 42: 307 8j Furuta T. Hirooka Y. Abe A. Sugata Y. Ueda M. Murakami K. Suzuki T. Tanaka K. Kan T. Bioorg. Med. Chem. Lett. 2007; 17: 3095 9a El-Telbani EM. J. Chem. Res. 2006; 11: 709 9b Zhu QH. Nie F. Feng JJ. Li YY. Wang XY. Xu YG. J. Heterocycl. Chem. 2016; 53: 919 10a Xie JW. Xu ML. Zhang RZ. Pan JY. Zhu WD. Adv. Synth. Catal. 2014; 356: 395 10b Zhang RZ. Meng CY. Xie JW. Xu ML. Zhu WD. Eur. J. Org. Chem. 2014; 3104 10c Zhang YR. Xie JW. Huang XJ. Zhu WD. Org. Biomol. Chem. 2012; 10: 6554 10d Fan L.-P. Li P. Li X.-S. Xu D.-C. Ge M.-M. Zhu W.-D. Xie J.-W. J. Org. Chem. 2010; 75: 8716 11a Seebach D. Angew. Chem., Int. Ed. Engl. 1979; 18: 239 11b Eisch JJ. J. Organomet. Chem. 1995; 500: 101 11c Pohl M. Lingen B. Muller M. Chem. Eur. J. 2002; 8: 5288 11d Wöhler F. Liebig J. Ann. Pharm. 1832; 3: 249 11e Lapworth A. J. Chem. Soc. 1903; 995 11f Breslow R. J. Am. Chem. Soc. 1958; 80: 3719 11g Stetter H. Kuhlmann H. In Organic Reactions . Vol. 40. Paquette LA. Wiley; New York: 1991: 407-496 11h Stetter H. Kuhlmann H. Chem. Ber. 1976; 109: 2890 11i Smith AB. III. Xian M. J. Am. Chem. Soc. 2006; 128: 66 12a Zeng XM. Meng CY. Bao JX. Xu DC. Xie JW. Zhu WD. J. Org. Chem. 2015; 80: 11521 12b Zeng XM. Xie JW. J. Org. Chem. 2016; 81: 3553 13a Revial G. Lim S. Viossat B. Lemoine P. Tomas A. Duprat AF. Pfau M. J. Org. Chem. 2000; 65: 4593 13b Palmieri A. Gabrielli S. Cimarelli C. Ballini R. Green Chem. 2011; 13: 3333 Zusatzmaterial Zusatzmaterial Supporting Information (PDF) (opens in new window) CIF File (ZIP) (opens in new window)
