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Thieno [2, 3-d] Pyrimidine-4-Ones. Part 4.* Directions of Reactions of the 2-Oxo-, -Thioxo-5, 6-Dimethyl-3, 4-Dihydrothieno [2, 3-d] Pyrimidine-4-Ones with Electrophilic Reagents

I. S. Ortikov, B. Zh. Elmuradov, Kh. M. Shakhidoyatov

Chemical Science International Journal · pp. 774–786 · Published 26 May 2014

10.9734/ACSJ/2014/10495

Abstract

Interaction of 5,6-dimethyl-3,4-dihydrothieno[2,3-d]pyrimidine-4-one (1), -thione(2) with alkylation agents (methyl-, ethyl-, n-propyl-, n-butyl iodides, allylbromide, benzyl chloride) in different conditions (in the presence of catalyst and/or without catalyst) were investigated. It was shown that methyl group in position 5 under action of nitrating mixture (NM) takes place aromatic ipso-substitution reaction or its oxidation up to corresponding carboxylic acid. Directions of reactions depend on nature of substituent in position N-3. It is revealed, that at absence of the substituent in position 3 (compounds 1, 2, 11) the electrophilic ipso-substitution of methyl group by nitro group with formation of 5-nitroderivatives took place. It is found, that at interaction of compounds 3, 19 with NM instead of substitution of methyl groups at C-5 go in an expected direction, i.e. there are oxidation of methyl groups.  

Thieno [2, 3-d] pyrimidine-4-ones alkylation nitrating mixture electrophilic ipso-substitution oxidation

References (20)

  1. 1 Synthesis and preliminary evaluation of some N-[5-(2-furanyl)-2-methyl-4-oxo-4H-thieno[2,3-d]pyrimidin-3-yl]-carboxamide and 3-substituted-5-(2-furanyl)-2-methyl-3H-thieno[2,3-d]pyrimidin-4-ones as antimicrobial agents [DOI]
  2. 2 Thienopyridines: synthesis, properties, and biological activity [DOI]
  3. 3 Synthesis, analgesic, anti-inflammatory, ulcerogenic index and antibacterial activities of novel 2-methylthio-3-substituted-5,6,7,8-tetrahydrobenzo (b) thieno[2,3-d]pyrimidin-4(3H)-ones [DOI]
  4. 4 Chemoenzymatic Synthesis of Pyrrolo[2,1-b]quinazolinones: Lipase-Catalyzed Resolution of Vasicinone [DOI]
  5. 5 Concise and Efficient Synthesis of Bioactive Natural Products Pegamine, Deoxyvasicinone, and (−)-Vasicinone [DOI]
  6. 6 Three-Step Total Synthesis of Pyrroloquinazolinoquinoline Alkaloid, Luotonin A, by Intramolecular Hetero Diels-Alder Reaction [DOI]
  7. 7 A short synthesis of quinazolinocarboline alkaloids rutaecarpine, hortiacine, euxylophoricine A and euxylophoricine D from methyl N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)anthranilates [DOI]
  8. 8 Synthesis and Antimicrobial Activity of New Pyridothienopyrimidines and Pyridothienotriazines [DOI]
  9. 9 Fused Pyrimidines. Part II: Synthesis and Antimicrobial activity of Some Furo[3,2-e]imidazo[1,2-c]pyrimidines and Furo[2,3-d]pyrimidines
  10. 10 Synthesis of 3,4-dihydroquinazolin-4-one: selenium-catalyzed reductive N-heterocyclization of N-(2-nitrobenzoyl)amides with carbon monoxide [DOI]
  11. 11 Synthesis of Substituted Thieno[2,3‐d]pyrimidin‐4‐ones and Their Testing for Evaluation of Cytotoxic Activity on Mammalian Cell Models [DOI]
  12. 12 A new synthesis of the cytotoxic alkaloid Luotonine A [DOI]
  13. 13 A Convenient Divergent Approach to the Alkaloids Isaindigotone and Luotonin A [DOI]
  14. 14 Reaction of 2,3-tetramethylen-3,4-dihydroquinazol-4-one and its derivatives with aromatic aldehydes and furfurol [DOI]
  15. 15 Synthesis and Bactericidal Activity of 6-H(nitro)-9-Arylidenedeoxyvasicinones and their Perchlorates [DOI]
  16. 16 Synthesis and antimicrobial activity of novel tetrahydrobenzothienopyrimidines [DOI]
  17. 17 ChemInform Abstract: A Convenient Divergent Approach to the Alkaloids Isaindigotone (III) and Luotonin A (VII). [DOI]
  18. 18 Synthesis and Biological Evaluation of Thieno Pyrimidine Derivatives
  19. 19 Synthesis of Isomeric Enamine Derivatives of Fused Cycloalkeno Thieno[2,3-d]pyrimidin-4(3H)-ones. Stereoelectronic Effect on the Regioselectivity [DOI]
  20. 20 Thieno[2,3-D]Pyrimidin-4-Ones. Part 3.* Electrophilic Ipso-Substitution Reactions Of Methyl And Methoxycarbonyl Groups [DOI]

Cited by 1

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Khurshed Bozorov, Jiang-Yu Zhao, Burkhon Elmuradov · European Journal of Medicinal Chemistry · 2015

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