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Vol. 23 No. 5 (2011): Vol 23 Issue 5

Synthesis of Di-(N-tropinonyl)pyridines and Di-(N-tropinonyl)benzenes

S.K. Choi1
1Department of Chemistry, Dong-A University, Saha-Gu, Busan 604-714, South Korea 2Department of Beautycare, Young-Dong University, Chungcheongbuk-do 370-701, South Korea *Corresponding author: Fax: +82 51 2007259; Tel: +82 51 2007249; E-mail: dijung@dau.ac.kr
J.H. Song1
1Department of Chemistry, Dong-A University, Saha-Gu, Busan 604-714, South Korea 2Department of Beautycare, Young-Dong University, Chungcheongbuk-do 370-701, South Korea *Corresponding author: Fax: +82 51 2007259; Tel: +82 51 2007249; E-mail: dijung@dau.ac.kr
E.J. Lee1
1Department of Chemistry, Dong-A University, Saha-Gu, Busan 604-714, South Korea 2Department of Beautycare, Young-Dong University, Chungcheongbuk-do 370-701, South Korea *Corresponding author: Fax: +82 51 2007259; Tel: +82 51 2007249; E-mail: dijung@dau.ac.kr
S.K. Jung1
1Department of Chemistry, Dong-A University, Saha-Gu, Busan 604-714, South Korea 2Department of Beautycare, Young-Dong University, Chungcheongbuk-do 370-701, South Korea *Corresponding author: Fax: +82 51 2007259; Tel: +82 51 2007249; E-mail: dijung@dau.ac.kr
K.Y. Jang1
1Department of Chemistry, Dong-A University, Saha-Gu, Busan 604-714, South Korea 2Department of Beautycare, Young-Dong University, Chungcheongbuk-do 370-701, South Korea *Corresponding author: Fax: +82 51 2007259; Tel: +82 51 2007249; E-mail: dijung@dau.ac.kr
Y.Y. Kim1
1Department of Chemistry, Dong-A University, Saha-Gu, Busan 604-714, South Korea 2Department of Beautycare, Young-Dong University, Chungcheongbuk-do 370-701, South Korea *Corresponding author: Fax: +82 51 2007259; Tel: +82 51 2007249; E-mail: dijung@dau.ac.kr
D.I. Jung1
1Department of Chemistry, Dong-A University, Saha-Gu, Busan 604-714, South Korea 2Department of Beautycare, Young-Dong University, Chungcheongbuk-do 370-701, South Korea *Corresponding author: Fax: +82 51 2007259; Tel: +82 51 2007249; E-mail: dijung@dau.ac.kr
J.T. Hahn2
1Department of Chemistry, Dong-A University, Saha-Gu, Busan 604-714, South Korea 2Department of Beautycare, Young-Dong University, Chungcheongbuk-do 370-701, South Korea *Corresponding author: Fax: +82 51 2007259; Tel: +82 51 2007249; E-mail: dijung@dau.ac.kr

Asian Journal of Chemistry, Vol. 23 No. 5 (2011): Vol 23 Issue 5

Abstract

As a part of a research program related to the synthetic study of pharmacologically interesting tropane compounds, we synthesized di-(Ntropinonyl) pyridines 7, 8, 9 and di-(N-tropinonyl)benzenes 12, 14. p-Dipyrrolylbenzene 10, 8-(4-pyrrol-1-yl-phenyl)-8- azabicyclo[3.2.1]octan-3-one 11 and 8-(3-pyrrol-1-yl-phenyl)-8-azabicyclo[3.2.1]-octan-3-one 13 as byproducts were synthesized. However, the reaction of 1,2-phenylene diamine with 2,5-dimethoxy tetrahydrofuran, acetone dicarboxylic acid and conc. HCl in water did not give 1,2-di-(8-azabicyclo[3.2.1]octan-3-onyl)benzene 15. We suppose that the major reason is the steric hindrance of tropane rings.

Keywords

Tropane alkaloids Di-(N-tropinonyl)pyridines Di-(N-tropinonyl)benzenes Anticonvulsant activity Steric hindrance.
Choi1, S., Song1, J., Lee1, E., Jung1, S., Jang1, K., Kim1, Y., … Hahn2, J. (2011). Synthesis of Di-(N-tropinonyl)pyridines and Di-(N-tropinonyl)benzenes. Asian Journal of Chemistry, 23(5), 2077–2080. Retrieved from https://asianpubs.org/index.php/ajchem/article/view/10333
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