An Easy Access to Novel Sugar-Based
Spirooxindole-pyrrolidines or -pyrrolizidines through [3+2] Cycloaddition
of Azomethine Ylides

Arasappan Hemamalini; Subbiah Nagarajan; Pawar Ravinder; Venkatesan Subramanian; Thangamuthu Mohan Das

doi:10.1055/s-0030-1260111

PAPER

An Easy Access to Novel Sugar-Based Spirooxindole-pyrrolidines or -pyrrolizidines through [3+2] Cycloaddition of Azomethine Ylides

Arasappan Hemamalini^a, Subbiah Nagarajan^a, Pawar Ravinder^b, Venkatesan Subramanian^b, Thangamuthu Mohan Das*^a
^a Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai - 600 025, India
Fax: +91(44)22352494; e-Mail: tmdas_72@yahoo.com;
^b Chemical Laboratory, Central Leather Research Institute (CSIR), Adyar, Chennai, 600 020, India

Abstract

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Abstract

An efficient one-pot synthesis of a library of novel sugar-based spirooxindole-pyrrolidines or -pyrrolizidines has been accomplished by [3+2] cycloaddition. This method utilizes an azomethine ylide derived from isatin and sarcosine or l-proline with an α,β-unsaturated β-C-glycosidic ketone as the dipolarophile. All these sugar-based heterocyclics were characterized by NMR (^¹H and ^¹³C), HPLC, and elemental analysis

Key words

4,6-O-butylidene-d-glucopyranose - α,β-unsaturated β-C-glycosidic ketones - cycloaddition - azomethine ylide - monospiroheterocyclics

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Referenzen

References

1a 1,3-Dipolar Cycloaddition Chemistry Vols. 1-2: Padwa A. Wiley; New York: 1984.

1b Grigg R. Sridharan V. In Advances in Cycloaddition Vol. 3: Curran DP. JAI Press; London: 1993. p.161

1c Kumar A. Pandey PS. Org. Lett. 2008, 10: 165

1d Karthikeyan K. Kumar RS. Muralidharan D. Perumal PT. Tetrahedron Lett. 2009, 50: 7175

1e Chaulagain MR. Aron ZD. J. Org. Chem. 2010, 75: 8271 ; and references cited therein

2a Zhou F. Liu Y.-L. Zhou J. Adv. Synth. Catal. 2010, 352: 1381

2b Thomson JE. Kyle AF. Ling KB. Smith SR. Slawin AMZ. Smith AD. Tetrahedron 2010, 66: 3801

2c Girgis AS. Eur. J. Med. Chem. 2009, 44: 91

2d Marti C. Carreira EM. Eur. J. Org. Chem. 2003, 2209

2e Galliford CV. Scheidt KV. Angew. Chem. Int. Ed. 2007, 46: 2

2f Shanmugam P. Viswambharan B. Selvakumar K. Madhavan S. Tetrahedron Lett. 2008, 49: 2611

3a Monlineux RJ. In Alkaloids: Chemical and Biological Perspectives Pelletier SW. Wiley; New York: 1987. Chap. 1.

3b Fujimori S. inventors; JP 882912. ; Chem Abstr. 1990, 112, 98409

4a Gasperi T. Loreto MA. Migliorini A. Ventura C. Eur. J. Org. Chem. 2011, 385

4b Chafeev M, Fu J, and Cadieux J.-J. inventors; US 20100331386.

4c Prasanna P. Balamurugan K. Perumal S. Yogeeswari P. Sriram D. Eur. J. Med. Chem. 2010, 45: 5653

4d Cadieux J.-J, Chafeev M, Chowdhury S, Douglas AF, Fu J, Langille J, Sun S, and Wood M. inventors; WO 2010078307.

4e Augustine T. Kanakam CC. Vithiya SM. Ramkumar V. Tetrahedron Lett. 2009, 50: 5906

4f Basavaiah D. Reddy RK. Org. Lett. 2007, 9: 57

5a Pellegrini C. Weber M. Borschberg H.-J. Helv. Chim. Acta 1996, 79: 151

5b Kamisaki H. Nanjo T. Tsukano C. Takemoto Y. Chem. Eur. J. 2011, 17: 626

5c White JD. Li Y. Ihle DC. J. Org. Chem. 2010, 75: 3569

6a Jossang A. Jossang P. Hadi HA. Sevenet T. Bodo B. J. Org. Chem. 1991, 56: 6527

6b Deppermann N. Thomanek H. Prenzel AHGP. Maison W. J. Org. Chem. 2010, 75: 5994

6c Klein JEMN. Perry A. Pugh DS. Taylor RJK. Org. Lett. 2010, 12: 3446

6d Reddy VJ. Douglas CJ. Tetrahedron 2010, 66: 4719

6e Reddy VJ. Douglas CJ. Org. Lett. 2010, 12: 952

6f Jaegli S. Vors J.-P. Neuville L. Zhu J. Synlett 2009, 2997

7 Anderton N. Cockrum PA. Colegate SM. Edgar JA. Flower K. Vit I. Willing RI. Phytochemistry 1998, 48: 437

8a Cui CB. Kakeya H. Osada H. Tetrahedron 1996, 52: 12651

8b Cui CB. Kakeya H. Osada H. J. Antibiot. 1996, 49: 832

8c Abou-Gharbia MA. Doukas PH. Heterocycles 1979, 12: 637

8d Kornet MJ. Thio AP. J. Med. Chem. 1976, 19: 892

9a Nagarajan S. Mohan Das T. Carbohydr. Res. 2009, 334: 1028

9b Nagarajan S. Mohan Das T. Arjun P. Raaman N. J. Mater. Chem. 2009, 19: 4587

9c Nagarajan S. Mohan Das T. New J. Chem. 2009, 33: 2391

9d Nagarajan S. Ravinder P. Subramanian V. Mohan Das T. New J. Chem. 2010, 34: 123

9e Nagarajan S. Anupa K. Babu V. Mohan Das T. Carbohydr. Res. 2010, 345: 1077

9f Karthik Kumar K. Elango M. Subramanian V. Mohan Das T. New J. Chem. 2009, 33: 1570

9g Nagarajan S. Arjun P. Raaman N. Mohan Das T. Carbohydr. Res. 2010, 345: 1988

9h Rajaganesh R. Jayakumar J. Sivaraj C. Raaman N. Mohan Das T. Carbohydr. Res. 2010, 345: 1649

9i Nagarajan S. Shanmugam MJ. Mohan Das T. Carbohydr. Res. 2011, 346: 722

10a Mellis RL. Mehltretter CL. Rist CE. J. Am. Chem. Soc. 1951, 73: 294

10b Bonner TG. Bourne EJ. Lewis D. J. Chem. Soc. 1965, 7453

11a Bragnier N. Scherrmann MC. Synthesis 2005, 814

11b Rodrigues F. Canac Y. Lubineau A. Chem. Commun. 2000, 2049

11c Riemann I. Papadopoulos MA. Knorst M. Fessner WD. Aust. J. Chem. 2002, 55: 147

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