Iron-catalyzed domino coupling reactions of π-systems

• Austin Pounder and
• William Tam

Beilstein J. Org. Chem. 2021, 17, 2848–2893, doi:10.3762/bjoc.17.196

• electron-withdrawing substituents on the oxime; however, the reaction required highly activated alkenes to proceed. 1,2-Disubstituted alkenes were tolerated and were diastereoselective for the anti-addition product. When maleimides 171 were used as the 2-carbon coupling partner, a [5 + 1] annulation was

Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation

• Xiaofeng Zhang,
• Kenny Pham,
• Shuai Liu,
• Marc Legris,
• Alex Muthengi,
• Jerry P. Jasinski and
• Wei Zhang

Beilstein J. Org. Chem. 2016, 12, 2204–2210, doi:10.3762/bjoc.12.211

• formaldehyde through [5 + 1] annulation to afford a novel polycyclic scaffold bearing tetrahydroquinazoline, pyrrolidine, pyrrolidinedione, and N-substituted maleimide in stereoselective fashion. Keywords: [5 + 1] annulation; [3 + 2] cycloaddition; one-pot reactions; stereoselective synthesis

• second [3 + 2] cycloaddition of azide compounds 2 with maleimides and sequential denitrogenation to products 7 is proposed in Scheme 2. 1,5-Diamino compounds 7 generated by one-pot reactions are good substrates for [5 + 1] annulation with aldehydes to form tetrahydroquinazolines 1 [34][35]. After

• exploring the reaction conditions, it was found that the reaction of 7a with formaldehyde in 1,4-dioxane at 110 °C afforded product 1a in 93% isolated yield (Table 2, entry 3). Other reactants such as HC(OEt)3, HCO2H, and paraformaldehyde (PFA) were also employed for the [5 + 1] annulation reactions. But

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

• ] anticancer, [5] anti-inflammatory, [6] anticonvulsant, [7] and antiproliferative activities as well as inhibitory effects for thymidylate synthase and poly-(ADP-ribose) polymerase (PARP). [8] An interesting method for quinazoline synthesis involved [5+1] annulation during the reaction of β-dicarbonyl