Synthesis of Some Substituted Adamantane-2,4-diones from 4, 4-disubstituted Cyclohexanone Enamines and Methacryloyl Chloride-Reference-Cited by-同舟云学术

Synthesis of Some Substituted Adamantane-2,4-diones from 4, 4-disubstituted Cyclohexanone Enamines and Methacryloyl Chloride

Published:2005-05 Issue:5 Volume:2005 Page:293-298
ISSN:1747-5198
Container-title:Journal of Chemical Research
language:en
Short-container-title:Journal of Chemical Research

Author:

Ahmed M. Giasuddin¹,Ahmed Syeda Asghari¹,Akhter Kawsari¹,Moeiz Syed M. Iqbal¹,Tsuda Yoshisuke²,Kiuchi Fumiyuki³,Hossain M. Mahmun⁴,Forsterling F. Holger⁴

Affiliation:

1. Department of Chemistry, University of Dhaka, Dhaka 1000, Bangladesh

2. Faculty of Pharmaceutical Sciences, Kanazawa University, 13-1 Takara-Machi, Kanazawa 920, Japan. Present address: H. E. J Research Institute of Chemistry, Karachi University, Pakistan

3. Department of Pharmacognosy, Graduate School of Pharmaceutical Science, Kyoto University, Yoshida, Sakyo-Ku, Kyoto 606-8501 Japan. Present address: Tsukuba Medicinal Plant Research Station, National Institute of Health Sciences, 1-Hachimandal, Tsukuba, Ibaraki 305-0843, Japan

4. Department of Chemistry, University of Wisconsin-Milwaukee, Milwaukee, WI 53201, USA

Abstract

The reaction of methacryloyl chloride with the morpholine enamine 4a derived from 4-acetyl-4-isopropenylcyclo-hexanone 3a gave 4,6-anti-6-hydroxy-5,6-dimethyl-7-isopropenyladamantane-2,4-dione 6a and 4,6-syn-6-hydroxy-5,6-dimethyl-7-isopropenyladamantane-2, 4-dione 7a as racemates epimeric at 6-C. Comparable results were found for the corresponding phenyl and benzyl substituted cyclohexanones 3b and 3c. In the case of the methyl-substituted cyclohexanone 3d 4,6- anti-alcohol 7d was isolated in pure form.

Publisher

SAGE Publications

Subject

General Chemistry

Link

http://journals.sagepub.com/doi/pdf/10.3184/0308234054323904

Reference26 articles.

1. Antiviral Activity of 1-Adamantanamine (Amantadine)

2. The in Vivo antiviral activity of 1-adamantanamine (amantadine)

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