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Synthesis 2022; 54(12): 2907-2915
DOI: 10.1055/a-1743-0191
DOI: 10.1055/a-1743-0191
paper
Ru(II)-Catalyzed C–H Activation and Alkyne Annulation Reaction of Phenyl Indandiones: Synthesis of Spirobi[indene]diones
The authors thank the Science and Engineering Research Board (SERB) and the Council of Scientific and Industrial Research (CSIR) New Delhi for financial support via the GPP-0367 (CRG/2019/001898) and OLP 2038 projects. B. R. Bora thanks DST for the INSPIRE-SRF fellowship.
Abstract
A Ru(II)-catalyzed synthesis of spirobi[indene]dione from phenyl indandione and alkyne is reported. This metal-catalyzed cyclization reaction proceeds through hydroxy group directed C(sp2)–H bond activation, keto–enol tautomerization and alkyne annulation pathways.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1743-0191. It contains copies of 1H NMR, 13C NMR, NOE and HRMS spectra of the synthesized compounds.
- Supporting Information
Publication History
Received: 13 August 2021
Accepted after revision: 17 January 2022
Accepted Manuscript online:
17 January 2022
Article published online:
28 March 2022
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References
- 1a Pandey RC, Toussaint MW, Stroshane RM, Kalita CC, Aszalos AA, Garretson AL, Wei TT, Byrne KM, Geoghegan RF, White RJ. J. Antibiot. 1981; 34: 1389
- 1b Blizzard TA, Morgan JD, Mosley RT, Birzin ET, Frisch K, Rohrer SP, Hammond ML. Bioorg. Med. Chem. Lett. 2003; 13: 479
- 1c Pizzirani D, Roberti M, Grimaudo S, Cristina AD, Pipitone RM, Tolomeo M, Recanatini M. J. Med. Chem. 2009; 52: 6936
- 1d Li F, Tartakoff SS, Castle SL. J. Am. Chem. Soc. 2009; 131: 6674
- 1e Chai Z, Rainey TJ. J. Am. Chem. Soc. 2012; 134: 3615
- 2 Rama Rao AV, Rao BV, Reddy DR, Singh AK. J. Chem. Soc., Chem. Commun. 1989; 400
- 3 Pandey B, Khire UR, Ayyangar NR. J. Chem. Soc., Chem. Commun. 1990; 1791
- 4 Moser WH, Zhang J, Lecher CS, Frazier TL, Pink M. Org. Lett. 2002; 4: 1981
- 5 Sánchez-Larios E, Holmes JM, Daschner CL, Gravel M. Org. Lett. 2010; 12: 5772
- 6a Gandeepan P, Müller T, Zell D, Cera G, Warratz S, Ackermann L. Chem. Rev. 2019; 119: 2192
- 6b Duarah G, Kaishap PP, Begum T, Gogoi S. Adv. Synth. Catal. 2019; 361: 654
- 6c Chidipudi SR, Khan I, Lam HW. Angew. Chem. Int. Ed. 2012; 51: 12115
- 6d Chidipudi SR, Burns DJ, Khan I, Lam HW. Angew. Chem. Int. Ed. 2015; 54: 13975
- 6e Dooley JD, Chidipudi SR, Lam HW. J. Am. Chem. Soc. 2013; 135: 10829
- 6f Zhao Y, He Z, Li S, Tang J, Gao G, Lan J, You J. Chem. Commun. 2016; 52: 4613
- 6g Stuart DR, Alsabeh P, Kuhn M, Fagnou K. J. Am. Chem. Soc. 2010; 132: 18326
- 7a Kaishap PP, Duarah G, Sarma B, Chetia D, Gogoi S. Angew. Chem. Int. Ed. 2018; 57: 456
- 7b Phukon J, Gogoi S. Chem. Commun. 2020; 56: 1133 ; and references cited therein
- 8 CCDC 2045360 (4g) 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
-
9a
Simmons EM,
Hartwig JF.
Angew. Chem. Int. Ed. 2012; 51: 3066
- 9b Seoane A, Casanova N, Quiñones N, Mascareñas JL, Gulías M. J. Am. Chem. Soc. 2014; 136: 834
- 9c Gómez-Gallego M, Sierra MA. Chem. Rev. 2011; 111: 4857
- 9d In parallel competition experiments, the reactions of 1a with 2a and 1a-D5 with 2a were performed simultaneously in separate reaction flasks under identical reaction conditions.
- 10 Allua S, Swamy KC. K. Adv. Synth. Catal. 2015; 357: 2665
- 11 Stadlbauer W, Fischer M. J. Heterocycl. Chem. 2002; 39: 131
- 12 Rosenfeld MJ, Ravi Shankar BK, Shechter H. J. Org. Chem. 1988; 53: 2699
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