Synthesis of Fused Pyrimido[1,6-a]indolones via Rhodium(III)-Catalyzed Cascade Annulations

Chada Raji Reddy; Srinivas Bodasu; Kathe Mallesh; Y. Lakshmi Prapurna

doi:10.1055/s-0040-1707312

Synthesis, Table of Contents

Synthesis 2021; 53(06): 1127-1136
DOI: 10.1055/s-0040-1707312

paper

Synthesis of Fused Pyrimido[1,6-a]indolones via Rhodium(III)-Catalyzed Cascade Annulations

Chada Raji Reddy ∗

^aDepartment of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India Email: rajireddy@iict.res.in

^bAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad 201 002, India

,

Srinivas Bodasu

^aDepartment of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India Email: rajireddy@iict.res.in

,

Kathe Mallesh

^aDepartment of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India Email: rajireddy@iict.res.in

^bAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad 201 002, India

,

Y. Lakshmi Prapurna

^aDepartment of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India Email: rajireddy@iict.res.in

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Abstract

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This work is dedicated to Dr. J. S. Yadav on the occasion of his 70^th 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]indolone

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References

References

For reviews, see:

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

For selected references, see:

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

For selected references, see:

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

For selected references, see:

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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