Three-component reaction of a δ-hydroxy-α,β-unsaturated aldehyde with arylamines and 1,3-diketones: A novel synthesis of oxa-aza bicycles

Synthesis

Volumn , Issue 10, 2010, Pages 1719-1723

  Reddy, Basi V Subba ^a   Divyavani, Ch ^a,b   Begum, Zubeda ^a   Yadav, Jhillu S ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b UNIVERSITY OF HYDERABAD   (India)

Author keywords

1,3 dicarbonyl compounds; Indium salts; Oxa aza bicycles; Perlin aldehyde

Indexed keywords

ARYL AMINES; DICARBONYL COMPOUNDS; DIKETONES; GOOD YIELD; HIGH SELECTIVITY; IN-SITU; INDIUM SALTS; OXA-AZA-BICYCLES; THREE COMPONENT REACTIONS; UNSATURATED ALDEHYDES;

ACETONITRILE; ALDEHYDES; BICYCLES; ESTERS; INDIUM; KETONES; SALTS; SUGAR (SUCROSE); SYNTHESIS (CHEMICAL); UNSATURATED COMPOUNDS;

INDIUM COMPOUNDS;

1,3 DICARBONYL DERIVATIVE; 1,3 DIKETONE; ACETONITRILE; ALDEHYDE; AMINOKETONE; AROMATIC AMINE; ESTER DERIVATIVE; INDIUM CHLORIDE; KETONE DERIVATIVE; MACROCYCLIC COMPOUND; OXA AZA BICYCLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 77952056908     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1218721     Document Type: Article

References (26)

1. Zhu J, Bienayme H, Multi-Component Reactions Wiley-VCH Weinheim 2005
2. Gonzalez F, Leasage S, Perlin A S., Carbohydr. Res. 1975 42 267
3. Mukhopadhyay A, Suryawanshi S N., Bhakuni D S., Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1988 27 1009
4. Sagar R, Pathak R, Shaw A K., Carbohydr. Res. 2004 339 2031; and references cited therein
5. Tulshian D B., Fraser-Reid B, J. Am. Chem. Soc. 1981 103 474
6. Tolstikov A G., Khakhalina N V., Spirikhin L V., Synthesis 1988 221
7. Pathak R, Shaw A K., Bhaduri A P., Chandrasekhar K V. G., Srivastava A, Srivastava K K., Chaturvedi V, Srivastava R, Srivastava B S., Arora S, Sinha S, Bioorg. Med. Chem. 2002 10 1695
8. Pathak R, Shaw A K., Bhaduri A P., Tetrahedron 2002 58 3535
9. Sagar R, Singh P, Kumar R, Maulik P R., Shaw A K., Carbohydr. Res. 2005 340 1287
10. Kaluza Z, Chmielewski M, Pedersen E B., Heterocycles 1988 27 1313
11. Wengel J, Lau J, Pedersen E B., Synthesis 1989 829
12. Lau J, Wengel J, Pedersen E B., Vestergaard B F., Synthesis 1991 1183
13. Wengel J, Pedersen E B., Vestergaard B F., Synthesis 1992 319
14. Singh S K., Parmar V S., Wengel J, Tetrahedron Lett. 1996 37 7619
15. Turner C I., Williamson R M., Turner P, Sherburn M S., Chem. Commun. 2003 1610; and references cited therein
16. Yadav J S., Reddy B V. S., Parimala G, Raju A K., Tetrahedron Lett. 2004 45 1543
17. Yadav J S., Reddy B V. S., Padmavani B, Synthesis 2004 405
18. Yadav J S., Sunitha V, Reddy B V. S., Das P P., Gyanchander E, Tetrahedron Lett. 2008 49 855
19. Yadav J S., Reddy B V. S., Satheesh G, Srinivasulu G, Kunwar A C., ARKIVOC 2005 (iii) 221
20. Yadav J S., Raju A K., Sunitha V, Tetrahedron Lett. 2006 47 5269
21. Yadav J S., Reddy B V. S., Satheesh G, Narasimhulu G, Portier Y, Madavi Ch, Kunwar A C., Tetrahedron Lett. 2008 49 3341
22. Yadav J S., Reddy B V. S., Srinivas M, Prabhakar A, Jagadeesh B, Tetrahedron Lett. 2004 45 6033
23. Yadav J S., Reddy B V. S., Srinivas M, Divyavani Ch, Kunwar A C., Madavi Ch, Tetrahedron Lett. 2007 48 8301
24. Yadav J S., Reddy B V. S., Satheesh G, Lakshmi P N., Kumar S K., Kunwar A C., Tetrahedron Lett. 2004 43 8587
25. Yadav J S., Reddy B V. S., Srinivas M, Divyavani Ch, Basha J, Sarma A V. S., J. Org. Chem. 2008 73 3252
26. Yadav J S., Reddy B V. S., Swamy D N., Lakshmi P N., Narsimhulu K, Srinivasulu G, Kunwar A C., Tetrahedron Lett. 2004 45 493