Ugi-type four-component reaction for a novel synthesis of 5-oxo-perhydrofuro[3, 2-b]pyran carboxylate derivatives

Tetrahedron Letters

Volumn 51, Issue 52, 2010, Pages 6835-6838

  Reddy, B V Subba ^a   Majumder, Nilanjan ^a   Gopal, A V Hara ^a   Chatterjee, Deepak ^a   Kunwar, A C ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Four component reaction; Furo 3,2 b pyran 5 one; Isocyanide; Meldrum's acid; Sugar hydroxyaldehyde

Indexed keywords

5 OXO PERHYDROFURO[ 3,2 B]PYRAN; ALCOHOL DERIVATIVE; CARBOHYDRATE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CYANIDE; DICHLOROMETHANE; HYDROXYALDEHYDE; ISOCYANIDE; MALONIC ACID DERIVATIVE; MELDRUM ACID; PYRAN DERIVATIVE; SECONDARY ALCOHOL; SUGAR HYDROXYALDEHYDE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; FOUR COMPONENT COUPLING REACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RING OPENING; ROOM TEMPERATURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 78650678759     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.10.083     Document Type: Article

References (19)

1. (a) Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123;
2. (b) Terret, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steel, J. Tetrahedron 1995, 51, 8135.
3. (a) Zhu, J.; Bienaymé, H. MulticomponentReactions; Wiley: Weinheim, 2005;
4. (b) Jiang, B.; Tu, S.-J.; Kaur, P.; Wever, W.; Li, G. J. Am. Chem. Soc. 2009, 131, 11660.
5. (a) Ugi, I. Angew. Chem., Int. Ed. Engl. 1982, 21, 810;
6. (b) Ugi, I.; Lohberger, S.; Karl, R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon press: Oxford, 1991; Vol. 2, p 1083.
7. Banfi, L.; Riva, R. Org. React. 2005, 65, 1.
8. (a) Dömling, A. Chem. Rev. 2006, 106, 17;
9. (b) Bienayme, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321.
10. (a) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3169;
11. (b) Nair, V.; Rajesh, C.; Vinod, A. U.; Bindu, S.; Sreekanth, A. R.; Mathess, J. S.; Balagopal, L. Acc. Chem. Res. 2003, 36, 899.
12. (a) Ramazani, A.; Mahyari, A. T.; Rouhani, M.; Rezaei, A. Tetrahedron Lett. 2009, 50, 5625;
13. (b) Sanudo, M.; Garcia-Valverde, M.; Marcaccini, S.; Delgado, J. J.; Rojo, J.; Torroba, T. J. Org. Chem. 2009, 74, 2189.
14. Shaabani, A.; Soleimani, E.; Rezayan, A. H.; Sarvary, A.; Khavasi, H. R. Org. Lett. 2008, 10, 2581.
15. (a) Yadav, J. S.; Reddy, B. V. S.; Narsimhaswamy, D.; Lakshmi, P. N.; Narsimulu, K.; Srinivasulu, G.; Kunwar, A. C. Tetrahedron Lett. 2004, 45, 3493;
16. (b) Yadav, J. S.; Reddy, B. V. S.; Singh, A. P.; Chaya, D. N.; Chatterjee, D.; Kunwar, A. C. Tetrahedron Lett. 2010, 50, 1478;
17. (c) Yadav, J. S.; Reddy, B. V. S.; Chandraiah, L.; Jagannadh, B.; Kiran Kumar, S.; Kunwar, A. C. Tetrahedron Lett. 2002, 43, 4527.
18. Bogatskii, A. V.; Gren, A. I.; Samitov, Yu. Yu.; Bogatskaya, E. D. Ekspermental'nayakhimiya 1970, 6, 530-537.
19. 9 (M+H): 538.2998. Found: 538.3086.