Microwave assisted synthesis of triazoloquinazolinones and benzimidazoquinazolinones

• Aboul-Fetouh E. Mourad,
• Ashraf A. Aly,
• Hassan H. Farag and
• Eman A. Beshr

Beilstein J. Org. Chem. 2007, 3, No. 11, doi:10.1186/1860-5397-3-11

• or a completely reduced pyrimidine nucleus are of interest, since they display valuable pharmaceutical activities. [1][2] There has been an increasing interest in the chemistry of 4(3H)-quinazolinones because of their biological significance. Many of them show antifungal, [3] antibacterial, [4

Tether- directed synthesis of highly substituted oxasilacycles via an intramolecular allylation employing allylsilanes

• Peter J. Jervis and
• Liam R. Cox

Beilstein J. Org. Chem. 2007, 3, No. 6, doi:10.1186/1860-5397-3-6

• precursors in hand, we were ready to conduct our intramolecular allylation study. Each aldehyde substrate (>95:5 d.r. in all four cases) was treated with TMSOTf in the presence of 2,4,6-tri-t-butyl pyrimidine (TTBP), [24] which acts as a Brønsted acid scavenger, in CH2Cl2 as solvent, conditions that had

The Elbs and Boyland- Sims peroxydisulfate oxidations

• E. J. Behrman

Beilstein J. Org. Chem. 2006, 2, No. 22, doi:10.1186/1860-5397-2-22

• synthesis of 5-hydroxyorotic acid from orotic acid is markedly affected by oxygen [5] but in a way opposite to the more usual observation that yields are improved by excluding oxygen. Here, in the absence of oxygen, yields are low and the pyrimidine ring undergoes cleavage to urea. Oxygen inhibits this side

Microwave- assisted ring closure reactions: Synthesis of 8-substituted xanthine derivatives and related pyrimido- and diazepinopurinediones

• Joachim C. Burbiel,
• Jörg Hockemeyer and
• Christa E. Müller

Beilstein J. Org. Chem. 2006, 2, No. 20, doi:10.1186/1860-5397-2-20

• -noradamantyl)carboxamido-6,8-dioxo-7-propyl-1,3,4,6,7,8-hexahydro-2H-pyrimido [1,6-a]pyrimidine (13) to the corresponding tricyclic derivative 5 was previously performed by heating it with HMDS under reflux conditions for 18 h [6]. We expected that microwave irradiation might shorten the reaction time here

• pyrimidopurine derivative 5 the addition of ammonium sulfate did not affect the reaction at all. Subsequently, we further investigated the scope of the method. We had previously demonstrated that pyrimido [1,6-a]pyrimidine derivatives like 13 and 15 could be converted to the tricyclic pyrimido [1,2,3-cd]purine

• -noradamantyl)carboxamido-6,8-dioxo-7-propyl-1,3,4,6,7,8-hexahydro-2H-pyrimido [1,6-a]pyrimidine (13) [6] (1.0 g, 8.4 mmol) in THF (3 ml) in a 10 ml pressure vial, HMDS (2 ml) was added. Microwave irradiation was applied (100 W, 140°C) for 20 min. The resulting yellow solution was hydrolyzed with 6 ml of

An efficient synthesis of novel pyrano[2,3-d]- and furopyrano[2,3-d]pyrimidines via indium- catalyzed multi- component domino reaction

• Dipak Prajapati and
• Mukut Gohain

Beilstein J. Org. Chem. 2006, 2, No. 11, doi:10.1186/1860-5397-2-11

• reaction of α,β-ethylenic ketones and ethyl vinyl ether or 2,3-dihydrofuran has remained unexplored.[11] Herein, we report the first example of indium(III) chloride catalysed synthesis of fused pyrimidine derivatives via a multicomponent domino Knoevenagel hetero Diels-Alder reaction. The reaction proceeds

• efficiently at ambient temperature in excellent yields (Scheme 1). Pyrimidine derivatives continue to be of great interest due to their wide range of biological activities.[12] Preparation of naturally occuring complex molecules containing a uracil ring pose significant synthetic challenges.[13] The

• , [19][20][21] most of which rely on multi-step reactions with yields being low. [22][23] The furo [2,3-d]pyrimidine derivatives act as useful sedatives, antihistamines, diuretics, muscle relaxants and antiulcer agents. Furthermore, pyrano [2,3-d]pyrimidines also represent broad classes of annelated

Crystal engineering of analogous and homologous organic compounds: hydrogen bonding patterns in trimethoprim hydrogen phthalate and trimethoprim hydrogen adipate

• Packianathan Thomas Muthiah,
• Savarimuthu Francis,
• Urszula Rychlewska and
• Beata Warżajtis

Beilstein J. Org. Chem. 2006, 2, No. 8, doi:10.1186/1860-5397-2-8

• Trimethoprim [2,4-diamino-5-(3',4',5'-trimethoxybenzyl)pyrimidine] is an antifolate drug. It selectively inhibits the bacterial dihydrofolate reductase (DHFR) enzyme. Results In the crystal structures of trimethoprim (TMP)-hydrogen phthalate (1) and trimethoprim-hydrogen adipate (2), one of the N atoms of the

• pyrimidine ring is protonated and it interacts with the deprotonated carboxylate oxygens through a pair of nearly parallel N-H...O hydrogen bonds to form a fork-like interaction. In the compound 1, the pyrimidine moieties of the TMP cations are centrosymmetrically paired through a pair of N-H...N hydrogen

• bonds involving 4-amino group and the N (N3) atom of the pyrimidine rings to form a 8-membered hydrogen bonded ring [R22(8)]. The 4-amino group of one TMP moiety and 2-amino group of another TMP moiety (both moieties are members of a base pair) are bridged by the carbonyl oxygen of the phthalate moiety

One-pot synthesis of novel 1H-pyrimido[4,5-c][1,2]diazepines and pyrazolo[3,4-d]pyrimidines

• Dipak Prajapati,
• Partha P. Baruah,
• Baikuntha J. Gogoi and
• Jagir S. Sandhu

Beilstein J. Org. Chem. 2006, 2, No. 5, doi:10.1186/1860-5397-2-5

• heteroannulation of uracils usually require either forcing conditions[16][17] or relatively longer synthetic pathways.[18] Also, pyrazolo [3,4-d]pyrimidines are a class of naturally occurring fused uracils that possess a wide range of biological activity.[19] Allopurinol (6-dehydroxy-pyrazolo [3,4-d]pyrimidine

• pyrimidine derivative, which will not only increase the synthetic scope of this hitherto under-developed reaction, but it will expand the synthetic versatility of uracil derivatives and provide diversity in the nature of the heterocyclic motif in a targeted library of potential products. Results and

• , we have isolated the corresponding 2,4-dioxo-pyrazolo [3,4-d]pyrimidine 6a in 80% yield instead of the expected seven-membered pyrimido[1,2]diazepine 7 or any other product (Scheme 3). The structure of the product 6a thus obtained was confirmed unambiguously by high resolution spectral techniques. To