Iodoxybenzoic Acid (IBX): An Efficient and Novel Oxidizing Agent for the Aromatization of 1,4-Dihydropyridines

J. S. Yadav; B. V. S. Reddy; A. K. Basak; G. Baishya; A. Venkat Narsaiah

doi:10.1055/s-2005-918519

PAPER

Iodoxybenzoic Acid (IBX): An Efficient and Novel Oxidizing Agent for the Aromatization of 1,4-Dihydropyridines [1]

J. S. Yadav*, B. V. S. Reddy, A. K. Basak, G. Baishya, A. Venkat Narsaiah
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: yadavpub@iict.res.in; e-Mail: +91(40)27160512;

Abstract

All articles of this category

Abstract

Hantzsch 1,4-dihydropyridines undergo smooth aromatization catalyzed by iodoxybenzoic acid (IBX) to afford the corresponding pyridine derivatives in high yields. All the reactions were carried out in DMSO solvent at 80-85 °C for a period of two to four hours to complete conversion of the substrates.

Keywords

hypervalent iodine reagents - dihydropyridines - aromatization - DMSO - pyridine derivatives

Full Text

References

1

IICT Communication No. 041107.

2a Varvoglis A. Hypervalent Iodine in Organic Synthesis Academic Press; London: 1997.

2b Stang PJ. J. Org. Chem. 2003, 68: 2997

2c Frigerio M. Santagostino M. Sputore S. J. Org. Chem. 1999, 64: 4537

2d Dess BD. Martin JC. J. Org. Chem. 1983, 48: 4155

2e Hartman C. Meyer V. Ber. Dtsch. Chem. Ges. 1893, 26: 1727

3a Nicolaou KC. Mathison CJN. Montagnon T. J. Am. Chem. Soc. 2004, 126: 5192

3b Yadav JS. Reddy BVS. Basak AK. Narsaiah AV. Tetrahedron 2004, 60: 2131

3c Frigerio M. Santagostino M. Tetrahedron Lett. 1994, 35: 8019

3d Frigerio M. Santagostino M. Sputore S. Palmissano G. J. Org. Chem. 1995, 60: 7272

3e Nicolaou KC. Montagnon T. Baran PS. Zhong YL. J. Am. Chem. Soc. 2002, 124: 2245

3f Nicolaou KC. Baran PS. Zhong YL. Vega JA. Angew. Chem. Int. Ed. 2000, 39: 2525

3g Bose DS. Srinivas P. Gurjar MK. Tetrahedron Lett. 1997, 38: 5839

4a Brewster ME. Simay A. Czako K. Winwood D. Fatag H. Bodor N. J. Org. Chem. 1989, 54: 3721

4b Friedlos F. Knox R. J. Biochem. Pharmacol. 1992, 44: 631

4c Stout DM. Meyers AI. Chem. Rev. 1982, 82: 223

4d Janis RA. Triggle DJ. J. Med. Chem. 1983, 25: 775

4e Wei XY. Rulledge A. Triggle DJ. J. Mol. Pharmacol. 1989, 35: 541

4f Bocker RH. Guengerich FP. J. Med. Chem. 1986, 28: 1596

5a Wehinger E, Meyer H, and Benz U. inventors; Ger. Offen., DE 3209276. ; Chem. Abstr. 1984, 100, 22580; Chem. Abstr. 1984, 100, 51454

5b Balogh M, Hermecz I, Kulcsar G, Meszaros Z, Virag S, Szutz T, and Sebestyen G. inventors; Belg. Patent, 889340. ; Chem. Abstr. 1982, 96, 85541

5c Treibs W. Beger J. Ann. 1962, 652: 192

5d Ciba Ltd. . inventors; Neth. Patent Appl., 6414307. ; Chem. Abstr. 1966, 64, 714

5e Yadav JS. Reddy BVS. Basak AK. Narsaiah AV. Green Chem. 2003, 5

6a Kurtz JL. Hutton R. Westheimer FH. J. Am. Chem. Soc. 1961, 33: 584

6b Zhu XQ. Zhao BJ. Chang JP. J. Org. Chem. 2000, 65: 8158

6c Yadav JS. Reddy BVS. Sabitha G. Garudammagari S. Reddy KK. Synthesis 2000, 1532

6d Bocker RH. Guengerich FP. J. Med. Chem. 1986, 28: 1596

6e Itoh T. Nagata K. Okada M. Ohsawa A. Tetrahedron Lett. 1995, 36: 2269

6f Balogh M. Hermecz I. Meszaros Z. Laszlo P. Helv. Chim. Acta 1984, 67: 2270

6g Maquestiau A. Mayence A. Eynde JJV. Tetrahedron Lett. 1991, 32: 3839

6h Anniyappan M. Muralidharan D. Perumal TP. Tetrahedron 2002, 58: 5069

6i Pfister JR. Synthesis 1990, 689

6j Eynde JJV. Mayence A. Maquestiau A. Tetrahedron 1992, 48: 463

7a Yadav JS. Reddy BVS. Basak AK. Narsaiah AV. Tetrahedron Lett. 2003, 44: 2217

7b Yadav JS. Reddy BVS. Sadashiv K. Harikishan K. Narsaiah AV. J. Mol. Catal. A. 2004, 220: 153

7c Yadav JS. Reddy BVS. Reddy PSR. Basak AK. Narsaiah AV. Adv. Synth. Catal. 2004, 346: 77

7d Yadav JS. Reddy BVS. Basak AK. Narsaiah AV. Prabhakar A. Jagadeesh B. Tetrahedron Lett. 2005, 46: 639

7e Yadav JS. Reddy BVS. Baishya G. Narsaiah AV. Chem. Lett. 2005, 1: 102