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-00000083.xml
Synlett 2015; 26(10): 1417-1421
DOI: 10.1055/s-0034-1380514
DOI: 10.1055/s-0034-1380514
letter
Silver-Prompted Carbonitration of Acrylamides for the Synthesis of Nitrating Oxindoles
Weitere Informationen
Publikationsverlauf
Received: 05. Februar 2015
Accepted after revision: 06. März 2015
Publikationsdatum:
02. April 2015 (online)
Abstract
A silver-prompted carbonitration of alkenes involving concomitant direct C–H functionalization and C–N bond formation to synthesize nitrating oxindoles has been developed. The CR TH2 receptor antagonist skeleton can be obtained from one of the products with further modification.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380514.
- Supporting Information
-
References
-
1a Zhou F, Liu Y.-L, Zhou J. Adv. Synth. Catal. 2010; 352: 1381
-
1b Galliford CV, Scheidt KA. Angew. Chem. Int. Ed. 2007; 46: 8748
- 1c Marti C, Carreira EM. Eur. J. Org. Chem. 2003; 2209
- 1d Millemaggi A, Taylor RJ. K. Eur. J. Org. Chem. 2010; 4527
- 1e Klein JE. M. N, Taylor RJ. K. Eur. J. Org. Chem. 2011; 6821
- 2a Barrett AG. M, Graboski GG. Chem. Rev. 1986; 86: 751
- 2b Ono N In The Nitro Group in Organic Synthesis . John Wiley and Sons; Hoboken: 2002
- 2c Feuer H, Nielson AT. Nitro Compounds: Recent Advances in Synthesis and Chemistry. VCH; Weinheim: 1990
- 3a Evans P, Grigg R, Ramzan MI, Sridharan V, York M. Tetrahedron Lett. 1999; 40: 3021
- 3b Anwar U, Casaschi A, Grigg R, Sansano JM. Tetrahedron 2001; 57: 1361
- 4a Jaegli SP, Dufour J, Wei H.-L, Piou T, Duan X.-H, Vors J.-P, Neuville L, Zhu J. Org. Lett. 2010; 12: 4498
- 4b Pinto A, Jia Y, Neuville L, Zhu J. Chem. Eur. J. 2007; 13: 961
- 4c Pinto A, Neuville L, Retailleau P, Zhu J. Org. Lett. 2006; 8: 4927
- 4d Piou T, Neuville L, Zhu J. Org. Lett. 2012; 14: 3760
- 4e Wei H.-L, Piou T, Dufour J, Neuville L, Zhu J. Org. Lett. 2011; 13: 2244
- 5a Mu X, Wu T, Wang H.-Y, Guo Y.-L, Liu G. J. Am. Chem. Soc. 2011; 134: 878
- 5b Wu T, Mu X, Liu G. Angew. Chem. Int. Ed. 2011; 50: 12578
- 6 Wei W.-T, Zhou M.-B, Fan J.-H, Liu W, Song R.-J, Liu Y, Hu M, Xie P, Li J.-H. Angew. Chem. Int. Ed. 2013; 52: 3638
- 7a Chu L, Qing FL. Chem. Commun. 2010; 46: 6285
- 7b Fu W, Guo W, Zou G, Xu C. J. Fluorine Chem. 2012; 140: 88
- 7c Kong W, Casimiro M, Merino E, Nevado C. J. Am. Chem. Soc. 2013; 135: 14480
- 7d Li L, Deng M, Zheng SC, Xiong YP, Tan B, Liu XY. Org. Lett. 2014; 16: 504
- 7e Lin JS, Liu XG, Zhu XL, Tan B, Liu XY. J. Org. Chem. 2014; 79: 7084
- 7f Wang F, Qi X, Liang Z, Chen P, Liu G. Angew. Chem. Int. Ed. 2014; 53: 1881
- 7g Wei W, Wen J, Yang D, Liu X, Guo M, Dong R, Wang H. J. Org. Chem. 2014; 79: 4225
- 7h Yang F, Klumphu P, Liang YM, Lipshutz BH. Chem. Commun. 2014; 50: 936
- 7i Xu P, Xie J, Xue Q, Pan C, Cheng Y, Zhu C. Chem. Eur. J. 2013; 19: 14039
- 7j Tang XJ, Thomoson CS, Dolbier WR. Org. Lett. 2014; 16: 4594
- 7k Zhang L, Li Z, Liu ZQ. Org. Lett. 2014; 16: 3688
- 7l Fuentes N, Kong W, Fernández-Sánchez L, Merino E, Nevado C. J. Am. Chem. Soc. 2015; 137: 964
- 7m Kong W, Fuentes N, García-Domínguez A, Merino E, Nevado C. Angew. Chem. Int. Ed. 2015; 54: 2487
- 7n Fan J.-H, Wei W.-T, Zhou M.-B, Song R.-J, Li J.-H. Angew. Chem. Int. Ed. 2014; 53: 6650
- 8a Zhou M.-B, Wang C.-Y, Song R.-J, Liu Y, Wei W.-T, Li J.-H. Chem. Commun. 2013; 49: 10817
- 8b Li Z, Zhang Y, Zhang L, Liu ZQ. Org. Lett. 2014; 16: 382
- 8c Fabry DC, Stodulski M, Hoerner S, Gulder T. Chem. Eur. J. 2012; 18: 10834
- 8d Fu W, Xu F, Fu Y, Zhu M, Yu J, Xu C, Zou D. J. Org. Chem. 2013; 78: 12202
- 8e Xie J, Xu P, Li H, Xue Q, Jin H, Cheng Y, Zhu C. Chem. Commun. 2013; 49: 5672
- 8f Lu MZ, Loh TP. Org. Lett. 2014; 16: 4698
- 8g Dai Q, Yu J, Jiang Y, Guo S, Yang H, Cheng J. Chem. Commun. 2014; 50: 3865
- 8h Zhou SL, Guo LN, Wang S, Duan XH. Chem. Commun. 2014; 50: 3589
- 8i Zhou SL, Guo LN, Wang H, Duan XH. Chem. Eur. J. 2013; 19: 12970
- 8j Zhou B, Hou W, Yang Y, Feng H, Li Y. Org. Lett. 2014; 16: 1322
- 8k Xu Z, Yan C, Liu ZQ. Org. Lett. 2014; 16: 5670
- 8l Shi L, Wang Y, Yang H, Fu H. Org. Biomol. Chem. 2014; 12: 4070
- 8m Bunescu A, Wang Q, Zhu J. Chem. Eur. J. 2014; 20: 14633
- 8n Zhou MB, Wang CY, Song RJ, Liu Y, Wei WT, Li JH. Chem. Commun. 2013; 49: 10817
- 8o Wu C.-Y, Deng G.-B, Hu M, Wei W.-T, Li J.-H. Synthesis 2014; 46: 2585
- 8p Zhang J.-L, Liu Y, Song R.-J, Jiang G.-F, Li J.-H. Synlett 2014; 25: 1031
- 8q Fan J.-H, Zhou M.-B, Liu Y, Wei W.-T, Ouyang X.-H, Song R.-J, Li J.-H. Synlett 2014; 25: 657
- 9a Li Y.-M, Shen Y, Chang K.-J, Yang S.-D. Tetrahedron 2014; 70: 1991
- 9b Li YM, Sun M, Wang HL, Tian QP, Yang SD. Angew. Chem. Int. Ed. 2013; 52: 3972
- 10a Yuan Y, Shen T, Wang K, Jiao N. Chem. Asian J. 2013; 8: 2932
- 10b Qiu J, Zhang R. Org. Biomol. Chem. 2014; 12: 4329
- 10c Matcha K, Narayan R, Antonchick AP. Angew. Chem. Int. Ed. 2013; 52: 7985
- 10d Kong W, Merino E, Nevado C. Angew. Chem. Int. Ed. 2014; 53: 5078
- 11a Meng Y, Guo LN, Wang H, Duan XH. Chem. Commun. 2013; 49: 7540
- 11b Zhou Z.-Z, Hua H.-L, Luo J.-Y, Chen Z.-S, Zhou P.-X, Liu X.-Y, Liang Y.-M. Tetrahedron 2013; 69: 10030
- 12a Wang H, Guo L.-N, Duan X.-H. Org. Lett. 2013; 15: 5254
- 12b Wang H, Guo L.-N, Duan X.-H. Adv. Synth. Catal. 2013; 355: 2222
- 12c Xu X, Tang Y, Li X, Hong G, Fang M, Du X. J. Org. Chem. 2013; 79: 446
- 12d Wang G, Wang S, Wang J, Chen S.-Y, Yu X.-Q. Tetrahedron 2014; 70: 3466
- 12e Ouyang X.-H, Song R.-J, Li J.-H. Eur. J. Org. Chem. 2014; 3395
- 12f Wang H, Guo LN, Duan XH. Chem. Commun. 2013; 49: 10370
- 12g Zhou M.-B, Song R.-J, Ouyang X.-H, Liu Y, Wei W.-T, Deng G.-B, Li J.-H. Chem. Sci. 2013; 4: 2690
- 12h Li Y.-H. Wang J.-J., Wei X.-H., Yang S.-D.; Chin. J. Org. Chem.; DOI: 10.6023/cjoc201412030.
- 13a Li YM, Wei XH, Li XA, Yang SD. Chem. Commun. 2013; 49: 11701
- 13b Shen T, Yuan Y, Jiao N. Chem. Commun. 2014; 50: 554
- 13c Li Y.-M, Shen Y, Chang K.-J, Yang S.-D. Tetrahedron Lett. 2014; 55: 2119
- 14a Wang JY, Zhang X, Bao Y, Xu YM, Cheng XF, Wang XS. Org. Biomol. Chem. 2014; 12: 5582
- 14b Tian Q, He P, Kuang C. Org. Biomol. Chem. 2014; 12: 6349
- 14c Shen T, Yuan Y, Song S, Jiao N. Chem. Commun. 2014; 50: 4115
- 14d Wang J.-Y, Su Y.-M, Yin F, Bao Y, Zhang X, Xu Y.-M, Wang X.-S. Chem. Commun. 2014; 50: 4108
- 14e Wei W, Wen J.-W, Yang D.-S, Du J, You J.-M, Wang H. Green Chem. 2014; 16: 2988
- 15a Yin F, Wang X.-S. Org. Lett. 2014; 16: 1128
- 15b Chen J.-R, Yu X.-Y, Xiao W.-J. Synthesis 2015; 47: 604
- 16a Marqués-López E, Merino P, Tejero T, Herrera RP. Eur. J. Org. Chem. 2009; 2401
- 16b Palomo C, Oiarbide M, Laso A. Eur. J. Org. Chem. 2007; 2561
- 17 Felluga F, Ghelfi F, Pitacco G, Roncaglia F, Valentin E, Venneri CD. Tetrahedron: Asymmetry 2010; 21: 2183
For reviews, see:
For reviews, see:
For selected references, see:
For selected references, see: