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Synthesis 2021; 53(06): 1127-1136
DOI: 10.1055/s-0040-1707312
DOI: 10.1055/s-0040-1707312
paper
Synthesis of Fused Pyrimido[1,6-a]indolones via Rhodium(III)-Catalyzed Cascade Annulations
C.R.R. thanks the Science and Engineering Research Board (SERB), New Delhi, for funding the project (EMR/2016/006253). Y.L.P. thanks Department of Science and Technology (DST) for a financial grant under Women Scientists Scheme-A [WOS-A, Grant No. SR/WOS-A/CS-1034/2014 (G)]. S.B. and K.M. thank the Council of Scientific and Industrial Research (CSIR), New Delhi, for research fellowships.
This work is dedicated to Dr. J. S. Yadav on the occasion of his 70th birthday for his contributions to organic synthesis
Abstract
A novel method for the synthesis of fused pyrimido[1,6-a]-indolone derivatives by annulation of 2-alkynylaryl aldehydes/2-alkynylarylidene ketones with N-(pivaloyloxy)-1H-indole-1-carboxamide catalyzed by rhodium has been accomplished. The reaction proceeds through C–H activation based annulation with alkyne moiety followed by addition of nitrogen on to aldehyde/activated alkene to give the products in moderate to good yields. Highly fluorescent dipyrrinone analogues could be synthesized from the derived products.
Key words
N-(pivaloyloxy)-1H-indole-1-carboxamide - C–H activation - aza-Michael addition - cascade annulation - pyrimido[1,6-a]indoloneSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707312. Copies of 1H and 13C NMR spectra for all new compounds are provided.
- Supporting Information
Publication History
Received: 07 August 2020
Accepted after revision: 04 September 2020
Article published online:
12 October 2020
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References
- 1a Ishikura M, Abe T, Choshi T, Hibino S. Nat. Prod. Rep. 2015; 32: 1389
- 1b Zi W, Zuo Z, Ma D. Acc. Chem. Res. 2015; 48: 702
- 1c Singh AK, Raj V, Saha S. Eur. J. Med. Chem. 2017; 142: 244
- 2a Wang Z, Addepalli Y, He Y. Org. Lett. 2018; 20: 644
- 2b Cai J, Wu B, Rong G, Zhang C, Qui L, Xu X. Org. Lett. 2018; 20: 2733
- 2c Xie C-C, Tan R, Liu Y-K. Org. Chem. Front. 2019; 6: 919
- 3a Hammer H, Winterfeldt E. Tetrahedron 1981; 37: 3609
- 3b Kato M, Nishino S, Ito K, Yamakuni H, Takasugi H. Chem. Pharm. Bull. 1994; 42: 2556
- 3c Kamata J, Okada T, Kotake Y, Niijima J, Nakamura K, Uenaka T, Yamaguchi A, Tsukara K, Nagasu T, Koyanagi N, Kitoh K, Yoshimatsu K, Yoshino H, Sugumi H. Chem. Pharm. Bull. 2004; 52: 1071
- 4a Mizuta M, Seio K, Ohkubo A, Miyata K. J. Org. Chem. 2007; 72: 5046
- 4b Mizuta M, Seio K, Ohkubo A, Sekine M. J. Phy. Chem. B 2009; 113: 9562
- 4c Dell’Acqua M, Ronda L, Piano R, Pellegrino S, Clerici F, Rossi E, Mozzarelli A, Gelmi M, Abbiati G. J. Org. Chem. 2015; 80: 10939
- 5a Zhang Y, Zheng J, Cui S. J. Org. Chem. 2014; 79: 6490
- 5b Zhang L.-B, Zhu M.-H, Du W.-B, Ni S.-F, Wen L.-R, Li M. Chem. Commun. 2019; 55: 14383
- 5c Wu Z.-J, Li y.-Q, Huang Z.-Z. Eur. J. Org. Chem. 2016; 5399
- 5d Chen X, Hu X, Bai S, Deng Y, Jiang H, Zeng W. Org. Lett. 2016; 18: 192
- 6a Facoetti D, Abbiati G, d’Avolio L, Ackermann L, Rossi E. Synlett 2009; 2273
- 6b Zheng J, Zhang Y, Cui S. Org. Lett. 2014; 16: 3560
- 6c Tao L, Shi M. Org. Lett. 2019; 21: 129
- 6d Hussain M, Chen M, Yang S, Wang G.-W. Org. Lett. 2019; 21: 8568
- 6e Zhang L.-B, Zhu M.-H, Ni S.-F, Wen L.-R, Li M. ACS Catal. 2019; 9: 1680
- 7 Reddy CR, Yarlagadda S, Sridhar B, Reddy BV. S. Eur. J. Org. Chem. 2017; 5763
- 8a Satoh T, Miura M. Chem. Eur. J. 2010; 16: 11212
- 8b Hyster TK, Rovis T. J. Am. Chem. Soc. 2010; 132: 10565
- 8c Pham MV, Ye B, Cramer N. Angew. Chem. Int. Ed. 2012; 51: 10610
- 8d Chuang S.-C, Gandeepan P, Cheng C.-H. Org. Lett. 2013; 15: 5750
- 8e Collins KD, Lied F, Glorius F. Chem. Commun. 2014; 50: 4459
- 8f Feng C, Feng D, Loh T-P. Chem. Commun. 2014; 50: 9865
- 8g Zhang X, Si W, Bao M, Asao N, Yamamoto Y, Jin T. Org. Lett. 2014; 16: 4830
- 8h Reddy Chidipudi S, Burns DJ, Khan I, Lam HW. Angew. Chem. Int. Ed. 2015; 54: 13975
- 8i Xu Y, Yang X, Zhou X, Kong L, Li X. Org. Lett. 2017; 19: 4307
- 8j Upadhyay NS, Thorat VH, Sato R, Annamalai P, Chuang S.-C, Cheng C.-H. Green Chem. 2017; 19: 3219
- 8k Li Y, Pi R, Ouyang X-H, Song R-J, Li J-H. Org. Lett. 2019; 21: 397
- 9a Guimond N, Gouliaras C, Fagnou K. J. Am. Chem. Soc. 2010; 132: 6908
- 9b Guimond N, Gorelsky SI, Fagnou K. J. Am. Chem. Soc. 2011; 133: 6449
- 10a Wang H, Glorius F. Angew. Chem. Int. Ed. 2012; 51: 7318
- 10b Yu D-G, de Azambuja F, Gennsch T, Daniliuc CG, Glorius F. Angew. Chem. Int. Ed. 2014; 53: 9650
- 10c Fukui Y, Liu P, Liu Q, He Z-T, Wu N-Y, Tian P, Lin G-Q. J. Am. Chem. Soc. 2014; 136: 15607
- 10d Webb NJ, Marsden SP, Raw SA. Org. Lett. 2014; 16: 4718
- 10e Semakul N, Jackson KE, Paton RS, Rovis T. Chem. Sci. 2017; 8: 1015
- 10f Hong SY, Jeong J, Chang S. Angew. Chem. Int. Ed. 2017; 56: 2408
- 11a Reddy CR, Mallesh K. Org. Lett. 2018; 20: 150
- 11b Reddy CR, Mallesh K, Srinivas B, Reddy DR. J. Org. Chem. 2020; 85: 7905
- 12a Reddy C, Kajare RC, Punna N. Chem. Commun. 2020; 56: 3445
- 12b Reddy CR, Sathish P, Valleti RR. ChemistrySelect 2019; 4: 8229
- 13a Brower JO, Lightner DA. J. Org. Chem. 2002; 67: 2713
- 13b Boiadjiev SE, Lightner DA. Tetrahedron: Asymmetry 2004; 15: 3301
- 13c Woydziak ZR, Boiadjiev SE, Norona WS, McDonagh AF, Lightner DA. J. Org. Chem. 2005; 70: 8417
- 14a Kaiser RP, Hessler F, Mosinger J, Cisarova I, Kotora M. Chem. Eur. J. 2015; 21: 13577
- 14b Hashmi AS. K, Buhrle M, Salathe R, Bats JW. Adv. Synth. Catal. 2008; 350: 2059
- 14c Hamze A, Provot O, Alami M, Brion J-D. Org. Lett. 2005; 7: 5625
- 14d Mora-Radó H, Bialy L, Czechtizky W, Méndez M, Harrity JP. A. Angew. Chem. Int. Ed. 2016; 55: 5834
- 14e Buksnaitiene R, Urbanaite A, Cikotiene I. J. Org. Chem. 2014; 79: 6532
- 15a Nishida M, Shintani R. Chem. Eur. J. 2019; 25: 7475
- 15b Zhou F, Han X, Lu X. J. Org. Chem. 2011; 76: 1491
- 15c Ji K, Zheng Z, Wang Z, Zhang L. Angew. Chem. Int. Ed. 2015; 54: 1245
- 15d Wu X, Li M-L, Chen D-F, Chen S-S. J. Org. Chem. 2014; 79: 4743
- 15e Huple DB, Ghorpade S, Liu R-S. Chem. Eur. J. 2013; 19: 12965
- 15f Onishi Y, Iyoda M, Nakagawa M. Tetrahedron Lett. 1981; 22: 3641
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For selected references, see:
For selected references, see: