Synthesis of 1,4-dihydropyridine using microwave-assisted aza-Diels-Alder reaction and its application to Amlodipine

Youn A. Lee; Seok Chan Kim

Journal of Industrial and Engineering Chemistry, Vol.17, No.3, 401-403, May, 2011

DOI10.1016/j.jiec.2011.02.031 Export Citation

Synthesis of 1,4-dihydropyridine using microwave-assisted aza-Diels-Alder reaction and its application to Amlodipine

Youn A. Lee, and Seok Chan Kim^†

Department of Bio & Nano Chemistry, Kookmin University, Seoul 136-702, Republic of Korea

E-mail:

We synthesized 1,4-dihydropyridine skeleton using aza-Diels-Alder reaction under the microwave irradiation conditionwhich has become a powerfulmethod for the rapid synthesis of a variety of organic molecules. The prepared 1,4-dihydropyridine product was further converted to antihypertensive drug Amlodipine to test this new methodology.

Keywords:1,4-Dihydropyridine;Amlodipine;Aza-Diels.Alder reaction;Microwave-assisted reaction

[References]

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[1] Triggle DJ, Lang DA, Janis RA, Med. Res. Rev., 9, 123 (1989)

[2] Goldmann S, Stoltefuss J, Angew. Chem. Int. Ed. Engl., 30, 1559 (1991)

[3] Siva Lakshmi Devi A, Srinivasa Rao Y, Satish M, Jyothi G, Babu Rao K, Omdutt T, Magn. Reson. Chem., 45, 688 (2007)

[4] Gotrane D, Deshmukh R, Ranade P, Sonawane S, Bhawal B, Gharpure M, Gurjar M, Org. Process Res. Dev., 14, 640 (2010)

[5] Ha¨ntzsch A, Justus Liebigs Ann. Chem., 215, 1 (1882)

[6] Alajarin R, Vaquero JJ, Garcia Navio JL, Alvarez-Builla J, Synlett, 297 (1992)

[7] Khadilkar BM, Gaikar VG, Chitnavis AA, Tetrahedron Lett., 36, 8083 (1995)

[8] Khadilkar BM, Chitnavis AA, Indian J. Chem. Sect. B., 34, 652 (1995)

[9] O¨ hberg L, Westman J, Synlett., 1293 (2001)

[10] Kim S, Choi K, Cheong C, Bull. Korean Chem. Soc., 23, 143 (2002)

[11] Campbell SF, US. Patent 4,572,909 (1986)

[12] Sircar L, Anderson KR, Tetrahedron Lett., 29, 6835 (1988)