Skip to content
Research Article Open access CC BY 3.0

Thieno[2,3-d ]Pyrimidin-4-Ones. Part 2*. Condensation of 2,3- Disubstituted Thieno[2,3-d]Pyrimidin-4-Ones with Aldehydes

B. Zh. Elmuradov, Kh. A. Bozorov, Kh. M. Shakhidoyatov

Chemical Science International Journal · pp. 164–177 · Published 1 Apr 2013

10.9734/ACSJ/2013/2966

Abstract

The reactions of 2,3-tri-,-tetramethylene-7,8–dihydro-6Н–thieno[2,3-d]pyrrolo[1,2-a] pyrimidine-4-ones (1a,b) and 2,3-dimethyl-,-tri-,-tetra-,-pentamethylene-6,7,8,9-tetrahydropyrido[1,2-a]thieno[2,3-d]pyrimidine–4-ones (4a-d), containing active methylene groups in positions 8 or 9, with aromatic aldehydes under acidic and alkaline conditions go depending on reaction conditions and nature of aromatic aldehydes with the formation of new (±)-(4-nitrophenyl) (2,3-tri, tetramethylene-7,8-dihydropyrrolo[1,2-a]thieno[2,3-d] pyrimidine-4-one-8-yl) methanol’s (2,3), 9-arylidene derivatives (5a-e – 8a-e) and (±) - (4 - nitrophenyl) (2,3-tetramethylene-6,7,8,9- tetrahydropyrido[1,2-a]thieno[2,3-d]pyrimidine–4–one-9-yl)methanol (9). If aldehydes with electron-withdrawing (nitro) group are used, the reaction can be stopped at a stage where the products of electrophilic addition reactions are racemates, i.e. containing asymmetric carbon atom in position 8 or 9, and if aromatic aldehydes with electron-donating substituent are used 9-arylidene derivatives are formed exclusively.

Condensed thieno[2,3-d]pyrimidin-4-ones electrophilic addition products 9-arylidene derivatives aldehydes condensation

References (31)

  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 Novel 5-Substituted 2,4-Thiazolidinedione and 2,4-Oxazolidinedione Derivatives as Insulin Sensitizers with Antidiabetic Activities [DOI]
  3. 3 Antimicrobial and antitumor activity of n-heteroimmine-1,2,3-dithiazoles and their transformation in triazolo-, imidazo-, and pyrazolopirimidines [DOI]
  4. 4 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]
  5. 5 Synthesis and biological evaluation of thieno[2,3-d]pyrimidine derivatives for anti-inflammatory, analgesic and ulcerogenic activity [DOI]
  6. 6 A novel entry into a new class of spiroheterocyclic framework: regioselective synthesis of dispiro[oxindole-cyclohexanone]pyrrolidines and dispiro[oxindole-hexahydroindazole]pyrrolidines [DOI]
  7. 7 Parallel synthesis and biological evaluation of 5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidin-4(3H)-one cytotoxic agents selective for p21-deficient cells [DOI]
  8. 8 Synthesis and antimicrobial activity of some novel thienopyrimidines and triazolothienopyrimidines [DOI]
  9. 9 Synthesis, Characterization and Biological Studies of Some Novel Thieno[2,3-d]pyrimidines [DOI]
  10. 10 Synthesis, Reactions, and Antimicrobial Evaluation of Some Polycondensed Thienopyrimidine Derivatives [DOI]
  11. 11 Synthesis and antiinflammatory activity of some pyrimidines and thienopyrimidines using 1-(2-Benzo[d][1,3]dioxol-5-yl)vinyl)-4-mercapto-6-methylpyrimidine-5-yl)ethan-2-one as a starting material [DOI]
  12. 12 Synthesis of Polynuclear Heterocyclic Compounds Derived from Thieno[2,3-d]pyrimidine Derivatives [DOI]
  13. 13 Synthesis of Substituted Thieno[2,3‐d]pyrimidin‐4‐ones and Their Testing for Evaluation of Cytotoxic Activity on Mammalian Cell Models [DOI]
  14. 14 C–C (alkynylation) vs C–O (ether) bond formation under Pd/C–Cu catalysis: synthesis and pharmacological evaluation of 4-alkynylthieno[2,3-d]pyrimidines [DOI]
  15. 15 Regioselective synthesis and biological evaluation of some novel thiophene-containing heterocyclic scaffolds as potential chemotherapeutic agents [DOI]
  16. 16 Synthesis of some novel 2-mercapto-3-(substituted amino)-5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-ones as analgesic and anti-inflammatory agents [DOI]
  17. 17 Synthesis, Characterization and Antibacterial Activities of New Pd(II) And Pt(IV) Complexes of Some Unsymmetrical Tetradentate Schiff Bases [DOI]
  18. 18 Mgo Enriched Coal Fly Ash As Highly Active Heterogeneous Base Catalyst For Claisen-Schmidt Condensation Reaction [DOI]
  19. 19 Synthesis of Some Novel Thieno[2, 3‐d] pyrimidines and their Antibacterial Activity [DOI]
  20. 20 New route to 2-arylthieno[2,3-d]pyrimidin-4(3H)-ones and isolation of the unoxidized intermediates [DOI]
  21. 21 Reaction of 2,3-tetramethylen-3,4-dihydroquinazol-4-one and its derivatives with aromatic aldehydes and furfurol [DOI]
  22. 22 Directions of reactions of 6-amino-, -acetylamino-, and -benzoylaminodeoxyvasicinones with aldehydes [DOI]
  23. 23 2-Acylmethyl-1H-benzimidazoles in the Biginelli Reaction [DOI]
  24. 24 New Synthesis of Tetrahydrobenzo (4,5) Thieno (2,3d) Pyrimidine Derivatives and Schiff Bases Derived from 2-aminotetrahydro Benzothiophenes and Hetarylcarboxaldehydes Studies on Their Antitumor and Antimicrobial Activities
  25. 25 A Simple Synthesis of Rutaecarpine [DOI]
  26. 26 ChemInform Abstract: A Simple Synthesis of Rutaecarpine. [DOI]
  27. 27 Lithiation of deoxypeganine and chiral synthesis of deoxypeganine derivatives [DOI]
  28. 28 Reactions of 5‐[3‐(Trifluoromethyl)phenyl]furan‐2‐carbaldehyde. [DOI]
  29. 29 Synthesis and Some Transformations of 2-(3-Amino-1-Phenylpropyl)furan [DOI]
  30. 30 Three‐Component Reaction of 2‐Aminobenzothiazole with Methylene‐Active Carbonyl Compounds and Aldehydes. [DOI]
  31. 31 Synthesis, Reactivity and Biological Activity of 17β-HSD1 Inhibitors Based on a Thieno[2,3-d]pryrimidin-4(3H)-one Core

Cited by 4

The Reactions of Hydrochlorides of 2, 3-Tri (Tetra) Methylene-3, 4-Dihydropyrimidine-4-Ones with N-Bromosuccinimide and Bromine

N. I. Mukarramov, Kh. Z. Khakimova, A. O. Nasrullaev, Kh. U. Khodjaniyazov, Kh. M. Shakhidoyatov · Chemical Science International Journal · 2013

Thieno[2,3-d]Pyrimidine-4-Ones. Part 5.# Hydrogen Chloride Promoted Synthesis of 2-Substituted Thieno[2,3-d]Pyrimidine-4-Ones and their Structural Investigations

D. Kh. Akramov, B. B. Zhurayev, B. A. Urakov, B. Zh. Elmuradov · Chemical Science International Journal · 2016

Article metrics

Real usage data collected on this platform.

20

Page views

0

PDF downloads

3

Outbound clicks

4

Citations

Views over time

Views by country

Approximate, from request IP at view time — not citizenship or institution. Countries with fewer than 5 views are grouped as "Other".

Traffic sources

Referring site, by host.

Views and downloads exclude known bots/crawlers. Citations combines this platform's own DOI-resolved index with each external source's own reported total — see Cited by above for individually listed citing works. Last refreshed 0 seconds ago.