Three-Component Reaction of
a δ-Hydroxy-α,β-Unsaturated Aldehyde
with Arylamines and 1,3-Diketones: A Novel Synthesis of Oxa-Aza
Bicycles

Basi V. Subba Reddy; Ch. Divyavani; Zubeda Begum; Jhillu S. Yadav

doi:10.1055/s-0029-1218721

PAPER

Three-Component Reaction of a δ-Hydroxy-α,β-Unsaturated Aldehyde with Arylamines and 1,3-Diketones: A Novel Synthesis of Oxa-Aza Bicycles

Basi V. Subba Reddy*^a, Ch. Divyavani^a,b, Zubeda Begum^a, Jhillu S. Yadav^a
^a Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160512; e-Mail: basireddy@iict.res.in;
^b IICT - An Associate Institution of the University of Hyderabad, Hyderabad 500007, India

Abstract

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Abstract

δ-Hydroxy-α,β-unsaturated sugar aldehydes (Perlin aldehydes) undergo smooth coupling with β-enamino ketones and β-enamino esters generated in situ from arylamines and 1,3-dicarbonyl compounds in the presence of 10 mol% InCl₃ in acetonitrile at 80 ˚C, to produce oxa-aza-bicycles in good yields with high selectivity.

Key words

Perlin aldehyde - 1,3-dicarbonyl compounds - indium salts - oxa-aza-bicycles

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Referenzen

References

1 Zhu J. Bienayme H. Multi-Component Reactions Wiley-VCH; Weinheim: 2005.

2a Gonzalez F. Leasage S. Perlin AS. Carbohydr. Res. 1975, 42: 267

2b Mukhopadhyay A. Suryawanshi SN. Bhakuni DS. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1988, 27: 1009

2c Sagar R. Pathak R. Shaw AK. Carbohydr. Res. 2004, 339: 2031 ; and references cited therein

3a Tulshian DB. Fraser-Reid B. J. Am. Chem. Soc. 1981, 103: 474

3b Tolstikov AG. Khakhalina NV. Spirikhin LV. Synthesis 1988, 221

3c Pathak R. Shaw AK. Bhaduri AP. Chandrasekhar KVG. Srivastava A. Srivastava KK. Chaturvedi V. Srivastava R. Srivastava BS. Arora S. Sinha S. Bioorg. Med. Chem. 2002, 10: 1695

3d Pathak R. Shaw AK. Bhaduri AP. Tetrahedron 2002, 58: 3535

3e Sagar R. Singh P. Kumar R. Maulik PR. Shaw AK. Carbohydr. Res. 2005, 340: 1287

4a Kaluza Z. Chmielewski M. Pedersen EB. Heterocycles 1988, 27: 1313

4b Wengel J. Lau J. Pedersen EB. Synthesis 1989, 829

4c Lau J. Wengel J. Pedersen EB. Vestergaard BF. Synthesis 1991, 1183

4d Wengel J. Pedersen EB. Vestergaard BF. Synthesis 1992, 319

4e Singh SK. Parmar VS. Wengel J. Tetrahedron Lett. 1996, 37: 7619

5 Turner CI. Williamson RM. Turner P. Sherburn MS. Chem. Commun. 2003, 1610 ; and references cited therein

6a Yadav JS. Reddy BVS. Parimala G. Raju AK. Tetrahedron Lett. 2004, 45: 1543

6b Yadav JS. Reddy BVS. Padmavani B. Synthesis 2004, 405

6c Yadav JS. Sunitha V. Reddy BVS. Das PP. Gyanchander E. Tetrahedron Lett. 2008, 49: 855

7a Yadav JS. Reddy BVS. Satheesh G. Srinivasulu G. Kunwar AC. ARKIVOC 2005, (iii): 221

7b Yadav JS. Raju AK. Sunitha V. Tetrahedron Lett. 2006, 47: 5269

8a Yadav JS. Reddy BVS. Satheesh G. Narasimhulu G. Portier Y. Madavi Ch. Kunwar AC. Tetrahedron Lett. 2008, 49: 3341

8b Yadav JS. Reddy BVS. Srinivas M. Prabhakar A. Jagadeesh B. Tetrahedron Lett. 2004, 45: 6033

8c Yadav JS. Reddy BVS. Srinivas M. Divyavani Ch. Kunwar AC. Madavi Ch. Tetrahedron Lett. 2007, 48: 8301

9a Yadav JS. Reddy BVS. Satheesh G. Lakshmi PN. Kumar SK. Kunwar AC. Tetrahedron Lett. 2004, 43: 8587

9b Yadav JS. Reddy BVS. Srinivas M. Divyavani Ch. Basha J. Sarma AVS. J. Org. Chem. 2008, 73: 3252

9c Yadav JS. Reddy BVS. Swamy DN. Lakshmi PN. Narsimhulu K. Srinivasulu G. Kunwar AC. Tetrahedron Lett. 2004, 45: 493