Superacid-Promoted Dual C–C Bond Formation by Friedel–Crafts Alkylation/Acylation of Cinnamate Esters: Synthesis of Indanones

Bokka Venkat Ramulu; Pedireddi Niharika; Gedu Satyanarayana

doi:10.1055/s-0034-1380385

Synthesis, Inhaltsverzeichnis

Synthesis 2015; 47(09): 1255-1268
DOI: 10.1055/s-0034-1380385

paper

Superacid-Promoted Dual C–C Bond Formation by Friedel–Crafts Alkylation/Acylation of Cinnamate Esters: Synthesis of Indanones

Autor*innen

Bokka Venkat Ramulu

Department of Chemistry, Indian Institute of Technology (IIT) Hyderabad, Ordnance Factory Estate Campus, Yeddumailaram – 502 205, Medak District, Andhra Pradesh, India eMail: gvsatya@iith.ac.in
Pedireddi Niharika

Department of Chemistry, Indian Institute of Technology (IIT) Hyderabad, Ordnance Factory Estate Campus, Yeddumailaram – 502 205, Medak District, Andhra Pradesh, India eMail: gvsatya@iith.ac.in
Gedu Satyanarayana*

Department of Chemistry, Indian Institute of Technology (IIT) Hyderabad, Ordnance Factory Estate Campus, Yeddumailaram – 502 205, Medak District, Andhra Pradesh, India eMail: gvsatya@iith.ac.in

Abstract

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Abstract

Dual C–C bond formation was accomplished in one pot for the synthesis of a wide variety of indanones mediated by triflic acid. The reaction proceeds via an initial Michael-addition-type Friedel–Crafts alkylation followed by intramolecular acylation (cyclization). Significantly, the method was also successfully employed on more reactive β-diarylcinnamates using slightly different conditions.

Key words

cinnamates - Friedel–Crafts - indanones - alkylation - benzophenones

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Referenzen

References

1a Tietze LF. Chem. Rev. 1996; 96: 115
1b Tietze LF, Beifuss U. Angew. Chem. 1993; 105: 137 ; Angew. Chem. Int. Ed. 1993, 32, 131

2 Bruggink A, Schoevaart R, Kieboom T. Org. Process Res. Dev. 2003; 7: 622

3a Johnson WS. Angew. Chem. 1976; 88: 33 ; Angew. Chem. Int. Ed. 1976, 15, 9
3b Leete E. Planta Med. 1990; 56: 339
3c Review: Heathcock CH. Angew. Chem. 1992; 104: 675 ; Angew. Chem. Int. Ed. 1992, 31, 665

4a Tietze LF, Wichmann J. Angew. Chem. 1992; 104: 1091 ; Angew. Chem. Int. Ed. 1992, 31, 1079
4b Tietze LF, Beifuss U, Ruther M, Rühlmann A, Antel J, Sheldrick GM. Angew. Chem. 1988; 100: 1200 ; Angew. Chem. Int. Ed. 1988, 27, 1186
4c Tietze LF, Beifuss U, Ruther M. J. Org. Chem. 1989; 54: 3120
4d Tietze LF, Beifuss U. Liebigs Ann. Chem. 1988; 321
4e Tietze LF, Beifuss U. Angew. Chem. 1985; 97: 1067 ; Angew. Chem. Int. Ed. 1985, 27, 1042
4f Tietze LF, Beifuss U. Org. Synth. 1992; 71: 167
4g Tietze LF, Rischer M. Angew. Chem. 1992; 104: 1269 ; Angew. Chem. Int. Ed. 1992, 31, 1221
4h Rueping M, Nachtsheim BJ. Beilstein J. Org. Chem. 2010; 75: 6

For reviews, see ref. 4h and:

5a Kobayashi S, Sugiura M, Kitagawa H, Lam WW.-L. Chem. Rev. 2002; 102: 2227
5b Poulsen TB, Jørgensen KA. Chem. Rev. 2008; 108: 2903
5c Sartori JM, Maggi R. Chem. Rev. 2011; 111: 181
5d Shi M, Lu J.-M, Wei Y, Shao L.-X. Acc. Chem. Res. 2012; 45: 641

6a Gore PH In Friedel–Crafts Related Reactions . Vol. III, Part I. Olah GA. John Wiley & Sons Inc; London: 1964: 1
6b Olah GA, Klumpp DA. Superelectrophiles and Their Chemistry . Wiley; New York: 2008

7a Sai KK. S, Tokarz MJ, Malunchuk AP, Zheng C, Gilbert TM, Klumpp DA. J. Am. Chem. Soc. 2008; 130: 14388
7b Zhang Y, Sheets MR, Raja EK, Boblak KN, Klumpp DA. J. Am. Chem. Soc. 2011; 133: 8467
7c Evans DA, Fandrick KR. Org. Lett. 2006; 8: 2249
7d Rose MD, Cassidy MP, Rashatasakhon P, Padwa A. J. Org. Chem. 2007; 72: 538
7e Wu Y.-C, Liu L, Liu Y.-L, Wang D, Chen Y.-J. J. Org. Chem. 2007; 72: 9383

8a Hashmi AS. K, Schwarz L, Choi J.-H. Angew. Chem. 2000; 112: 2382 ; Angew. Chem. Int. Ed. 2000, 39, 2285
8b Dyker G, Muth E, Hashmi AS. K, Ding L. Adv. Synth. Catal. 2003; 345: 1247
8c Hashmi AS. K, Schwarz L, Rubenbauer P, Blanco MC. Adv. Synth. Catal. 2006; 348: 705

9 Olah GA, Germain A, Lin HC, Forsyth DA. J. Am. Chem. Soc. 1975; 97: 2928
10 Rendy R, Zhang Y, McElrea A, Gomez A, Klumpp DA. J. Org. Chem. 2004; 69: 2340
11 Lee BH, Choi YL, Shin S, Heo J.-N. J. Org. Chem. 2011; 76: 6611

12a Wang LJ, Zhu HT, Wang AQ, Qiu YF, Liu XY, Liang YM. J. Org. Chem. 2014; 79: 204
12b Dethe DH, Murhade GM. Chem. Commun. 2013; 49: 8051

13a Taber DF, Tirunahari PK. Tetrahedron 2011; 67: 7195
13b Naredla RR, Klumpp DA. Chem. Rev. 2013; 113: 6905
13c Nguyen Q, Nguyen T, Driver TG. J. Am. Chem. Soc. 2013; 135: 620

14 Niharika P, Ramulu BV, Satyanarayana G. Org. Biomol. Chem. 2014; 12: 4347

15a Raja EK, DeSchepper DJ, Lill SO. N, Klumpp DA. J. Org. Chem. 2012; 77: 5788
15b Boblak KN, Klumpp DA. J. Org. Chem. 2014; 79: 5852
15c Klumpp DA, Baek DN, Prakash GK. S, Olah GA. J. Org. Chem. 1997; 62: 6666
15d Sai KK. S, Esteves PM, Penha ET. D, Klumpp DA. J. Org. Chem. 2008; 73: 6506

16a Bhar SS, Ramana MM. V. J. Org. Chem. 2004; 69: 8935
16b Womack GB, Angeles JG, Fanelli VE, Heyer CA. J. Org. Chem. 2007; 72: 7046
16c Prakash GK. S, Paknia F, Vaghoo H, Rasul G, Mathew T, Olah GA. J. Org. Chem. 2010; 75: 2219
16d Choi YL, Kim BT, Heo J.-N. J. Org. Chem. 2012; 77: 8762
16e Mahoney SJ, Moon DT, Hollinger J, Fillion E. Tetrahedron Lett. 2009; 50: 4706
16f Aikawa H, Tago S, Umetsu K, Haginiwa N, Asao N. Tetrahedron 2009; 65: 1774

17a Suzuki T, Ohwada T, Shudo K. J. Am. Chem. Soc. 1997; 119: 6774
17b Ohwada T, Suzuki T, Shudo K. J. Am. Chem. Soc. 1998; 120: 4629
17c Kurouchi H, Sugimoto H, Otani Y, Ohwada T. J. Am. Chem. Soc. 2010; 132: 807
17d Colquhoun HM, Lewis DF, Williams DJ. Org. Lett. 2001; 3: 2337
17e Fillion E, Fishlock D. Org. Lett. 2003; 5: 4653
17f Wang Q, Padwa A. Org. Lett. 2006; 8: 601
17g Chassaing S, Kumarraja M, Pale P, Sommer J. Org. Lett. 2007; 9: 3889
17h Saito A, Umakoshi M, Yagyu N, Hanzawa Y. Org. Lett. 2008; 10: 1783
17i Tang S, Xu Y, He J, He Y, Zheng J, Pan X, She X. Org. Lett. 2008; 10: 1855
17j Kangani CO, Day BW. Org. Lett. 2008; 10: 2645
17k Kim K, Kim I. Org. Lett. 2010; 12: 5314
17l Chinnagolla RK, Jeganmohan M. Org. Lett. 2012; 14: 5246
17m Eom D, Park S, Park Y, Ryu T, Lee PH. Org. Lett. 2012; 14: 5392

18a Ramulu BV, Reddy AG. K, Satyanarayana G. Synlett 2013; 24: 868
18b Das A, Reddy AG. K, Krishna J, Satyanarayana G. RSC Adv. 2014; 4: 13941

19a Srikrishna A, Srinivasa Rao M, Santosh J, Gharpure N, Babu Ch. Synlett 2001; 1986
19b Groundwater PW, Garnett I, Morton AJ, Sharif T, Coles SJ, Hursthouse BM, Anderson MJ, Bendell D, McKillop A, Zhang W. J. Chem. Soc., Perkin Trans. 1 2001; 2781
19c Deng J, Duan Z.-C, Huang J.-D, Hu X.-P, Wang D.-Y, Yu S.-B, Xu X.-F, Zheng Z. Org. Lett. 2007; 9: 4825
19d Chintareddy VR, Ellern A, Verkade JG. J. Org. Chem. 2010; 75: 7166
19e Srikrishna A, Reddy T, Kumar J, Praveen P, Vijaykumar D. Synlett 1996; 67
19f Tolochko AF, Dombrovskii AV. Ukr. Biokhim. Zh. (Russian Edition) 1965; 31: 220
19g Reddy AG. K, Mahendar L, Satyanarayana G. Synth.Commun. 2014; 44: 2076
19h Granger R, Orzalesi H, Favier JC, Muratelle A. C. R. Hebd. Seances Acad. Sci. 1961; 252: 3271

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