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
Article Published :
25 January 2011
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.
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Choi1, S.; Song1, J.; Lee1, E.; Jung1, S.; Jang1, K.; Kim1, Y.; Jung1, D.; Hahn2, J. Synthesis of Di-(N-tropinonyl)pyridines and Di-(N-tropinonyl)benzenes. ajc 2011 , 23 , 2077-2080.
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