RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2018; 50(08): 1667-1674
DOI: 10.1055/s-0036-1591758
DOI: 10.1055/s-0036-1591758
paper
Construction of Functionalized (Dihydro)thieno[2,3-c]chromene Derivatives via a Domino Michael Addition/Intramolecular Cyclization Reaction
We are grateful for the financial support by the Program for the National Natural Science Foundation of China (21272214).Weitere Informationen
Publikationsverlauf
Received: 05. Dezember 2017
Accepted after revision: 03. Januar 2018
Publikationsdatum:
29. Januar 2018 (online)
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
3-nitro-2H-chromenes - thioamides - domino reactions - thieno[2,3-c]chromenes - heterocyclesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591758.
- Supporting Information
- CIF File
-
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