Bismuth(III) Chloride: An Efficient Catalyst for the One-Pot Stereoselective Synthesis of Octahydroacridines

Gowravaram Sabitha; Erigala Venkata Reddy; Jhillu S. Yadav

doi:10.1055/s-2002-20045

PAPER

Bismuth(III) Chloride: An Efficient Catalyst for the One-Pot Stereoselective Synthesis of Octahydroacridines [1]

Gowravaram Sabitha*, Erigala Venkata Reddy, Jhillu S. Yadav
Organic Division I, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)7160512; e-Mail: sabitha@iict.ap.nic.in;

Abstract

All articles of this category

Abstract

A one-pot procedure for the stereocontrolled preparation of octahydroacridine derivatives is reported, which involves the intramolecular hetero-Diels-Alder reaction of N-arylimines produced in situ from citronellal and aromatic amines. The temperature of the reaction medium plays a key role in determination of the trans/cis ratio.

Key words

bismuth(III) chloride - diastereoselective - one-pot procedure - hetero-Diels-Alder reaction

Full Text

References

1

IICT Communication No: 010905.

2 Ermolaeva VG. Yashunskii VG. Polezhaeva AI. Mashkovskii MD. Khim.-Farm. Zh. 1968, 2: 20 ; Chem. Abstr. 1968, 69, 106517

3 Canas-Rodriguez A. Canas RG. Mateo-Bernardo A. An. Quim., Ser. C. 1987, 83: 24 ; Chem. Abstr. 1988, 108: 112191

4a Lafargue P. Moriniere JL. Pont P. Mennier J. C. R. Acad. Sci., Ser. C 1970, 270: 1186 ; Chem. Abstr. 1970, 72,132686

4b Schiiltz H. Ebel S. Fitz H. Arzneim.-Forsch. 1985, 35: 1015

5a Sakanishi K. Mochida I. Okazaki H. Soeda M. Chem. Lett. 1990, 319 ; and references cited therein

5b Nagai M. Bull. Chem. Soc. Jpn. 1991, 64: 330

5c Sakanishi K. Ohira M. Mochida I. Okazaki H. Soeda M. J. Chem. Soc., Perkin Trans. 2 1988, 1769

6 Tanaka J. Takabe K. Taniguchi K. Katagiri T. Nippon Kogaku Kaishi 1981, 1043 ; Chem. Abstr. 1981, 95, 219818

7 Sakane S. Matsumura Y. Yamamura Y. Ishida Y. Maruoka K. Yamamoto H. J. Am. Chem. Soc. 1983, 105: 672

8 Layer RW. Westfahal JC. J.Org. Chem. 1979, 44: 1146

9 Laschat S. Lauterwein J. J. Org. Chem. 1993, 58: 2856

10 Kiselyov AS. Smith LII. Armstrong RW. Tetrahedron 1998, 54: 5089

11a Review: Suzuki H. Ikegami T. Matano Y. Synthesis 1997, 249

11b Vidal S. Synlett 2001, 1194

12 Wada M. Takeichi E. Matsumoto T. Bull. Chem. Soc. Jpn. 1991, 69: 990

13 Laurent-Robert H. Garrigues B. Dubac J. Synlett 2000, 1160 ; and references cited therein

14a Repichet S. Le Roux C. Dubac J. Desmurs JR. Eur. J. Org. Chem. 1998, 2743

14b Orita A. Tanahashi C. Kakuda A. Otera J. Angew. Chem. Int. Ed. 2000, 39: 2877

15a Labruouillere M. Le Roux C. Oussaid A. Gaspard-Iloughmane H. Dubac J. Bull. Soc. Chim. Fr. 1995, 132: 522

15b Montero J.-L. Winum J.-Y. Leydet A. Kamal M. Pavia AA. Roque J.-P. Carbohydr. Res. 1997, 297: 175

16 The Organic Chemistry of Arsenic, Antimony and Bismuth Compounds Patai S. Wiley; New York: 1994.

17a Sabitha G. Satheesh Babu R. Venkata Reddy E. Srividya R. Yadav JS. Adv. Synth. Catal. 2001, 343: 169

17b Sabitha G. Satheesh Babu R. Venkata Reddy E. Yadav JS. Chem. Lett. 2000, 1074

18 Sabitha G. Venkata Reddy E. Yadav JS. Synthesis 2001, 1979

19a Tietze LF. Wichmann J. Angew.Chem., Int. Ed. Engl. 1992, 31: 1079

19b Laschat S. Kung H. J. Org. Chem. 1991, 56: 5883