Subscribe to RSS
DOI: 10.1055/a-1856-1905
Ultrasound-Assisted Rapid Synthesis of Functionalized 1,2-Teraryls by Ring Transformation Methodology
F.V.S. acknowledges CSIR New Delhi India [Grant No.: 02/(0330)/17-EMR-II] for the financial support.
![](https://www.thieme-connect.de/media/synthesis/202223/lookinside/thumbnails/ss-2022-m0224-op_10-1055_a-1856-1905-1.jpg)
Abstract
The function of styryl acetate as a carbanion nucleophile source has been explored in the ring transformation reaction of 2H-pyranones. The ultrasound-assisted carbanion-induced ring transformation of 4-amino-6-aryl-3-cyano-2H-pyran-2-ones using (E)-styryl acetate in the presence of KOH and DMF at room temperature is presented as an alternative strategy for the synthesis of functionalized 1,2-teraryls in high yields. This metal-free methodology provides easy access to a series of 1,2-teraryls and features broad functional group tolerance and mild reaction condition. Single crystal X-ray diffraction analysis of 4-(piperidin-1-yl)-6-(thiophen-2-yl)-[1,1′-biphenyl]-3-carbonitrile indicated that the crystal belongs to monoclinic system with a P21 space group having twisted aryl rings.
Key words
1,2-teraryls - ring transformation methodology - 2H-pyranones - ultrasound-assisted synthesis - terphenyls - metal-free reaction - carbanion-induced reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1856-1905.
- Supporting Information
Publication History
Received: 03 May 2022
Accepted after revision: 18 May 2022
Accepted Manuscript online:
18 May 2022
Article published online:
09 August 2022
© 2022. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1a Liu JK. Chem. Rev. 2006; 106: 2209
- 1b Trujillo JM, Jorge RE, Navarro E, Boada J. Phytochemistry 1990; 29: 2991
- 2 Pure and Functionalized Carbon Based Nanomaterials: Analytical, Biomedical, Civil and Environmental Engineering Applications. Zarzycki PK. CRC Press; Boca Raton: 2020
- 3a Miyamae T, Hashizume H, Ogawa T, Okayama T, Nukui E, Oshima K, Morikawa T, Hagiwara M. Arzneimittelforschung 1997; 47: 13
- 3b Hongou K, Miyamae T, Hashizume H, Oshima K, Ogawa T, Hongou T, Morikawa T, Hagiwara M. Arzneimittelforschung 1997; 47: 1104
- 4 Ohkanda J, Lockman JW, Kothare MA, Qian Y, Blaskovich MA, Sebti SM, Hamilton AD. J. Med. Chem. 2002; 45: 177
- 5a Mota González ML, Carrillo Castillo A, Ambrosio Lázaro RC, Flores Méndez J, Moreno M, Luque PA, Navarro D. J. Chem. 2017; DOI: DOI: 10.1155/2017/8275489.
- 5b Chandrasekar S, Singh FV. ChemistrySelect 2020; 5: 7452
- 5c Kanimozhi R, Singh FV. J. Mol. Struct. 2020; 1219: 128633
- 5d Umar S, Jha AK, Goel A. Asian J. Org. Chem. 2016; 5: 187
- 6a Park JY, McKenna GB. Phys. Rev. B Condens. Matter. 2000; 61: 6667
- 6b Abe K, Ushigoe Y, Yoshitake H, Yoshio MJ. Power Sources 2006; 153: 328
- 7a Goel A, Dixit M, Chaurasia S, Kumar A, Raghunandan R, Maulik PR, Anand RS. Org. Lett. 2008; 10: 2553
- 7b Goel A, Sharma A, Rawat M, Anand RS, Kant R. J. Org. Chem. 2014; 79: 10873
- 8 El Gemayel M, Narita A, Dössel LF, Sundaram RS, Kiersnowski A, Pisula W, Hansen MR, Ferrari AC, Orgiu E, Feng X, Müllen K, Samorì P. Nanoscale 2014; 6: 6301
- 9 Bhalla V, Tejpal R, Kumar M. Sensors Actuators B: Chem. 2010; 151: 180
- 10a Eckhardt H, Miller GG, Baughman RH. Synth. Met. 1984; 9: 441
- 10b Schiavon G, Zecchin S, Zotti G, Cattarin S. J. Electroanal. Chem. Interfacial Electrochem. 1986; 213: 53
- 11 Schneider DJ, Landis DA, Fleitz PA, Seliskar CJ, Kauffman JM, Steppel RN. Laser Chem. 1991; 11: 49
- 12 Adrio LA, Antelo Miguez JM, Hii KK. Org. Prep. Proced. Int. 2009; 41: 331
- 13a Motti E, Mignozzi A, Catellani M. J. Mol. Catal. A: Chem. 2003; 204–205: 115
- 13b Antelo Miguez JM, Adrio LA, Sousa-Pedrares A, Vila JM, Hii KK. J. Org. Chem. 2007; 72: 7771
- 13c Sharif M, Reimann S, Villinger A, Langer P. Synlett 2010; 913
- 13d Lu DD, He XX, Liu FS. J. Org. Chem. 2017; 82: 10898
- 13e Vuoti S, Autio J, Haukka M, Pursiainen J. Inorg. Chim. Acta 2009; 362: 4685
- 13f Tu J, Li G, Zhao X, Xu F. Tetrahedron Lett. 2019; 60: 44
- 13g Gu N, Liu Y, Liu P, Ma X, Liu Y. Synth. Commun. 2016; 46: 154
- 14 Brenna E, Fuganti C, Serra S. J. Chem. Soc., Perkin Trans. 1 1998; 901
- 15 Lim CH, Kim SH, Kim KH, Kim JN. Tetrahedron Lett. 2013; 54: 2476
- 16 Nogi K, Yorimitsu H. Chem. Commun. 2017; 53: 4055
- 17 Karmakar S, Mandal T, Dash J. Eur. J. Org. Chem. 2019; 5916
- 18a Pratap R, Sil D, Ram VJ. Tetrahedron Lett. 2005; 46: 5025
- 18b Pratap R, Kumar B, Ram VJ. Tetrahedron 2006; 62: 8158
- 18c Goel A, Kumar V, Hemberger Y, Singh FV, Nag P, Knauer M, Kant R, Raghunandan R, Maulik PR, Bringmann G. J. Org. Chem. 2016; 81: 10721
- 19 Singh S, Shally, Shaw R, Yadav R, Kumar A, Pratap R. RSC Adv. 2016; 6: 14768
- 20 Shetgaonkar SE, Singh FV. Synthesis 2018; 50: 3540
- 21 Singh FV, Kole PB. Synthesis 2019; 51: 1435
- 22 Shetgaonkar SE, Singh FV. Synth. Commun. 2019; 49: 1092
- 23 Subashini C, Kennedy LJ, Singh FV. J. Mol. Struct. 2021; 1226: 129365
- 24 Shetgaonkar SE, Singh FV. Synth. Commun. 2020; 50: 2511
- 25 Krishnan M, Singh FV. J. Mol. Struct. 2022; 1256: 132544
- 26a Singh FV, Kumar V, Goel A. Synlett 2007; 2086
- 26b Goel A, Singh FV, Verma D. Synlett 2005; 2027
- 26c Goel A, Singh FV, Sharon A, Maulik PR. Synlett 2005; 623
- 26d Goel A, Verma D, Singh FV. Tetrahedron Lett. 2005; 46: 8487
- 26e Goel A, Singh FV. Tetrahedron Lett. 2005; 46: 5585
- 26f Singh FV, Kumar A, Goel A. Tetrahedron Lett. 2006; 47: 7767
- 26g Kumar A, Singh FV, Goel A. Tetrahedron Lett. 2007; 48: 7283
- 26h Kumar A, Singh FV, Goel A. Tetrahedron Lett. 2007; 48: 8223
- 26i Kumar V, Singh FV, Parihar A, Goel A. Tetrahedron Lett. 2009; 50: 680
- 26j Singh FV, Dixit M, Chaurasia S, Raghunandan R, Maulik PR, Goel A. Tetrahedron Lett. 2007; 48: 8998
- 27a Poladura B, Martínez-Castañeda Á, Rodríguez-Solla H, Llavona R, Concellón C, Del Amo V. Org. Lett. 2013; 15: 2810
- 27b Kole P, Shetgaonkar S, Singh FV. Der Pharma Chem. 2017; 9: 10
- 28a Mohamed MA. J. Pharm. Res. Int. 2019; 31: 1
- 28b Puri S, Kaur B, Parmar A, Kumar H. Curr. Org. Chem. 2013; 17: 1790
- 28c Govindaraju S, Tabassum S, Khan RU. R, Pasha MA. Chem. Heterocycl. Compd. 2016; 52: 964
- 28d Reddy MB. M, Jayashankara VP, Pasha MA. Green Chem. Lett. Rev. 2013; 6: 107
- 28e Savun-Hekimoğlu B. Acoustics 2020; 2: 766
- 29a Mangaonkar SR, Shetgaonkar SE, Vernekar AA, Singh FV. ChemistrySelect 2020; 5: 10754
- 29b Singh FV, Mangaonkar SR, Kole PB. Synth. Commun. 2018; 48: 2169
- 30 CCDC 2162915 (3g) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures.
- 31 Demakov PA, Bogomyakov AS, Urlukov AS, Andreeva AY, Samsonenko DG, Dybtsev DN, Fedin VP. Materials 2020; 13: 1
- 32 Doucet H, Bruneau C, Dixneuf P. Synlett 1997; 807