American Chemical Science Journal, ISSN: 2249-0205,Vol.: 3, Issue.: 4 (October-December)

Original-research-article

Thieno[2,3-d]Pyrimidin-4-Ones. Part 3.* Electrophilic Ipso-Substitution Reactions of Methyl and Methoxycarbonyl Groups

 

B. Zh. Elmuradov^1*, Kh. A. Bozorov¹, А. Zh. Kurbanbayeva¹, I. S. Ortikov¹, Kh. M. Bobakulov¹, N. D. Abdullayev¹, A. Yili², H. A. Aisa² and Kh. Ðœ. Shakhidoyatov¹

¹Organic Synthesis Department, Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent 100170, Uzbekistan.
²Key Laboratory of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi, 830011, China.

Article Information

Editor(s):

(1) Sang Hak Lee, Professor, Department of Chemistry, Kyungpook National University, Daegu, 702-701, Korea.

Reviewers:

(1) Anonymous.

(2) Farouk M. E. Abdel-Megeid, National Research Centre, Egypt.

(3) Anonymous.

(4) Anonymous.

Complete Peer review History: http://www.sciencedomain.org/review-history/1659

Interactions of 5,6-dimethyl- (1), 3,5,6-trimethylthieno[2,3-d]pyrimidin-4(3H)-ones (2) and 2,3-dimethyl- (5-7), 2-methyl-3-methoxycarbonylthieno[2,3-d]dihydropyrrolo-, -tetrahydropyrido-, tetrahydroazepino[1,2-a]pyrimidin-4-ones (14-16) with nitrating mixture were investigated. For the first time it is shown, that in dependence on the presence of substituent in position 2 and 3 of pyrimidine and thiophene rings reaction goes in various directions; by electrophilic ipso-substitution of methyl groups at C-5 by nitro group, or its oxidation up to carboxyl groups with formation corresponding 5-carboxy derivatives. It is revealed, that at absence of the substituent in position 3 (compound 1) the electrophilic ipso-substitution of methyl group by nitro group with formation of 5-nitro derivative took place. It is found, that at interaction of compounds 2,5-7, 14-16 with nitrating mixture instead of substitution of methyl groups at C-2, goes in an unexpected direction, i.e. there are oxidation of methyl groups or electrophilic ipso-substitution of methoxycarbonyl groups in position 3 by nitro group.

Keywords :

thieno[2,3-d]pyrimidin-4-ones; nitrating mixture; electrophilic ipso-substitution; oxidation; methyl groups.

Full Article - PDF    Page 364-377

DOI : 10.9734/ACSJ/2013/4203

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