Regioselective Synthesis of
Highly Functionalized 3-Spiropyrrolidine/pyrrolizidine
Oxindoles and Acenaphthenones via One-Pot Four-Component [3+2] Cycloaddition

Kai Zhao; Song-Lei Zhu; Da-Qing Shi; Xiao-Ping Xu; Shun-Jun Ji

doi:10.1055/s-0029-1218731

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2010(11): 1793-1803
DOI: 10.1055/s-0029-1218731

PAPER

Regioselective Synthesis of Highly Functionalized 3-Spiropyrrolidine/pyrrolizidine Oxindoles and Acenaphthenones via One-Pot Four-Component [3+2] Cycloaddition

Kai Zhao, Song-Lei Zhu, Da-Qing Shi, Xiao-Ping Xu*, Shun-Jun Ji*
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. of China
Fax: +86(512)65880307; e-Mail: chemjsj@suda.edu.cn;

Further Information

Publication History

Received 13 January 2010
Publication Date:
12 April 2010 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

A facile and efficient entry into highly functionalized 3-spiropyrrolidine oxindoles and 3-spiropyrrolizidine oxindoles, as well as to 3-spiropyrrolidine acenaphthenones via one-pot four-component reactions of 3-cyanoacetylindoles, aldehydes, isatin/acenaphthylene-1,2-dione and amino acid has been developed. Particularly valuable features of this method include high yields of products, broad substrate scope and a straightforward procedure.

Key words

multicomponent [3+2] cycloaddition - spirooxindoles - one-pot synthesis - indole-containing heterocycles

References

1a Nair V. Rajesh C. Vinod AU. Bindu S. Sreekanth AR. Mathen JS. Balagopal L. Acc. Chem. Res. 2003, 36: 899

Google Scholar
1b Armstrong RW. Combs AP. Tempest PA. Brown SD. Keating TA. Acc. Chem. Res. 1996, 29: 123

Google Scholar
1c Tietze LF. Modi A. Med. Res. Rev. 2000, 20: 304

Google Scholar
1d Domling A. Ugi I. Angew. Chem. Int. Ed. 2000, 39: 3168

Google Scholar
1e Weber L. Curr. Med. Chem. 2002, 9: 2085

Google Scholar
2a Orru RVA. de Greef M. Synthesis 2003, 1471

Google Scholar
2b Domling A. Chem. Rev. 2006, 106: 17

Google Scholar
2c Feliu L. Vera-Luque P. Albericio F. Álvarez M. J. Comb. Chem. 2007, 9: 521

Google Scholar
2d Karthikeyan K. Perumal PT. Etti S. Shanmugam G. Tetrahedron 2007, 63: 10581

Google Scholar
2e Zhu J. Eur. J. Org. Chem. 2003, 1133

Google Scholar
2f Litvinov YM. Mortikov VY. Shestopalov AM. J. Comb. Chem. 2008, 10: 741

Google Scholar
2g Mohammadi AA. Dabiri M. Qaraat H. Tetrahedron 2009, 65: 3804

Google Scholar
2h Devi I. Kumar BSD. Bhuyan PJ. Tetrahedron Lett. 2003, 44: 8307

Google Scholar
3a da Silva JFM. Garden SJ. Pinto AC. J. Braz. Chem. Soc. 2001, 12: 273

Google Scholar
3b Monlineux RJ. In Alkaloids: Chemical and Biological Perspective Pelletier SW. Wiley; New York: 1987. Chap. 1.

Google Scholar
3c Fujimora S. inventors; Jap. Pat. Appl. 88-2912. Chem. Abstr. 1990, 112, 98409
3d Galliford CV. Scheidt KV. Angew. Chem. Int. Ed. 2007, 46: 8748

Google Scholar
3e Shanmugam P. Viswambharan B. Selvakumar K. Madhavan S. Tetrahedron Lett. 2008, 49: 2611

Google Scholar
4a Pajouhesh H. Parsons R. Popp FD. J. Pharm. Sci. 1983, 72: 318

Google Scholar
4b Popp FD. J. Heterocycl. Chem. 1984, 21: 1367

Google Scholar
4c Dandia A. Singh R. Khaturia S. Merienne C. Morgant G. Loupy A. Bioorg. Med. Chem. 2006, 14: 2409

Google Scholar
4d Chene P. Nat. Rev. Cancer 2003, 3: 102

Google Scholar
4e Ding K. Lu Y. Nikolovska-Coleska Z. Qiu S. Ding Y. Gao W. Stuckey J. Krajewski K. Roller PP. Tomita Y. Parrish DA. Deschamps JR. Wang S.
J. Am. Chem. Soc. 2005, 127: 10130

Google Scholar
5a Marti C. Carreira EM. Eur. J. Org. Chem. 2003, 2209

Google Scholar
5b Toyota M. Ihara M. Nat. Prod. Rep. 1998, 15: 327

Google Scholar
5c Lin H. Danishefsky SJ. Angew. Chem. Int. Ed. 2003, 42: 36

Google Scholar
5d Lo MM.-C. Neumann CS. Nagayama S. Perlstein EO. Schreiber SL. J. Am. Chem. Soc. 2004, 126: 16077

Google Scholar
5e Dounary AB. Hatanaka K. Kodanko JJ. Oestreich M. Pfeifer LA. Weiss MM. J. Am. Chem. Soc. 2003, 125: 6261 ; and references therein

Google Scholar
6 Skiles JW. McNeil D. Tetrahedron Lett. 1990, 31: 7277

Crossref Google Scholar
7a 1,3-Dipolar Cycloaddition Chemistry Padwa A. Wiley-Interscience; New York: 1984.

Google Scholar
7b Dondas HA. Fishwick CWG. Grigg R. Kilner C. Tetrahedron 2004, 60: 3473

Google Scholar
7c Boruah M. Konwar D. Sharma SD. Tetrahedron Lett. 2007, 48: 4535

Google Scholar
7d Kawashima K. Kakehi A. Noguchi M. Tetrahedron 2007, 63: 1630

Google Scholar
8a Watson AA. Fleet GWJ. Asano N. Molyneux RJ. Nash RJ. Phytochemistry 2001, 56: 265

Google Scholar
8b O’Hagan D. Nat. Prod. Rep. 1997, 637

Google Scholar
9a Horri S. Fukase H. Matsuo T. Kameda Y. Asano N. Matsui K. J. Med. Chem. 1986, 29: 1038

Google Scholar
9b Spearman MA. Jamieson JC. Wright JA. Exp. Cell Res. 1987, 168: 116

Google Scholar
9c Tsukamoto K. Uno A. Shimada S. Imokaw G. Clin. Res. 1989, 37A: 722

Google Scholar
9d Karpas A. Fleet GWJ. Dwek RA. Petursson S. Mamgoong SK. Ramsden NG. Jacob GS. Rademacher TW. Proc. Natl. Acad. Sci. U.S.A. 1988, 85: 9229

Google Scholar
10a Shanmugam P. Viswambharan B. Madhavan S. Org. Lett. 2007, 9: 4095

Google Scholar
10b Kathiravan S. Raghunathan R. Tetrahedron Lett. 2009, 50: 6116

Google Scholar
10c Shanmugam P. Vaithiyanathan V. Tetrahedron 2008, 64: 3322

Google Scholar
11a Suresh Babu AR. Raghunathan R. Tetrahedron Lett. 2008, 49: 4487

Google Scholar
11b Fokas D. Ryan WJ. Casebier DS. Coffen DL. Tetrahedron Lett. 1998, 39: 2235

Google Scholar
12 . Abdel-Aziz S. Heteroat. Chem. 2002, 13: 324

Crossref Google Scholar
13a Sundberg RJ. The Chemistry of Indoles Academic Press; New York: 1996.

Google Scholar
13b Shanthi G. Perumal PT. Tetrahedron Lett. 2008, 49: 7139

Google Scholar
13c Casapullo A. Bifulco G. Bruno I. Riccio R. J. Nat. Prod. 2000, 63: 447

Google Scholar
13d Bao B. Sun Q. Yao X. Hong J. Lee CO. Sim CJ. Im KS. Jung JH. J. Nat. Prod. 2005, 68: 711

Google Scholar
13e Skibo EB. Xing C. Dorr RT. J. Med. Chem. 2001, 44: 3545

Google Scholar
13f Gupta L. Talwar A. Palne NS. Gupta S. Chauhan PMS. Bioorg. Med. Chem. Lett. 2007, 17: 4075

Google Scholar
13g Kaniwa K. Arai MA. Li X. Ishibashi M. Bioorg. Med. Chem. Lett. 2007, 17: 4254

Google Scholar
14a Sridhar G. Gunasundari T. Raghunathan R. Tetrahedron Lett. 2007, 48: 319

Google Scholar
14b Periyasami G. Raghunathan R. Surendiran G. Mathivanan N. Bioorg. Med. Chem. Lett. 2008, 18: 2342

Google Scholar
14c Kumar RR. Perumal S. Senthilkumar P. Yogeeswari P. Sriram D. Tetrahedron 2008, 64: 2962

Google Scholar
15a Zhu S.-L. Ji S.-J. Zhang Y. Tetrahedron 2007, 49: 1777

Google Scholar
15b Zhu S.-L. Ji S.-J. Zhao K. Zhang Y. Lett. Org. Chem. 2008, 5: 319

Google Scholar
15c Zhu S.-L. Zhao K. Su X.-M. Ji S.-J. Synth. Commun. 2009, 39: 1355

Google Scholar
16a Zhu S.-L. Ji S.-J. Su X.-M. Sun C. Liu Y. Tetrahedron Lett. 2008, 49: 1777

Google Scholar
16b Zhu S.-L. Ji S.-J. Zhao K. Liu Y. Tetrahedron Lett. 2008, 49: 2578

Google Scholar
16c Zhao K. Xu X.-P. Zhu S.-L. Shi D.-Q. Zhang Y. Ji S.-J. Synthesis 2009, 2697

Google Scholar
For a detailed discussions on the mechanism of azomethine ylide formation by the decarboxylative route, see:
17a Ardill H. Dorrity MJR. Grigg R. Leon-Ling MS. Malone JF. Sridharan V. Thainpatanagul S. Tetrahedron 1990, 46: 6433

Google Scholar
17b Ardill H. Xavier LR. Grigg R. Montgomery J. Sridharan V. Surendrakumar S. Tetrahedron 1990, 46: 6449

Google Scholar

18

Structural parameters for 5b (CCDC 760960): Data collection: Rigaku Mercury CCD area detector; empirical formula: C₅₆H₄₂Cl₂N₈O₄; colorless solid; crystal dimensions: 0.55 × 0.50 × 0.15 mm; orthorhombic; space group: Pna21; unit cell dimensions: a = 16.2592(11) Å, b = 11.3924(9) Å, c = 25.3133(19) Å; V = 4688.8(6) Å^³; Mr 961.88; Z = 4; D(calcd) = 1.363 Mg/m^³; λ (Mo-K_α) = 0.71075 Å; µ = 0.197 mm^-¹; F(000) = 2000, 3.00˚ < θ < 25.49˚, R _[I>2 _σ ₍ _I)] = 0.0532, wR _[I>2 _σ ₍ _I)] = 0.1221; largest diff. peak and hole: 0.270 and -0.274 e Å^-³.

19

Structural parameters for 5f (CCDC 760959): Data collection: Rigaku Mercury CCD area detector; empirical formula: C₂₈H₂₂N₄O₂; colorless solid; crystal dimensions: 0.60 × 0.55 × 0.18 mm; monoclinic; space group P 21/c; unit cell dimensions: a = 25.720 (5) Å, b = 11.1847(18) Å, c = 16.399(3) Å, β = 105.649(5)˚; V = 4542.7(14) Å^³; Mr = 446.50; Z = 8; D(calcd) = 1.306 Mg/m^³; λ (Mo-K_α) = 0.71075 Å; µ = 0.084 mm^-¹; F(000) = 1872, 3.05˚ < θ < 25.50˚, R _[I>2s ₍ _I)] = 0.0790, wR _[I>2s ₍ _I)] = 0.2030; largest diff. peak and hole: 0.397 and -0.269 e Å^-³.