Microwave‐Assisted [3+2] Cycloaddition and Suzuki–Miyaura Cross‐Coupling for a Concise Access to Polyaromatic Scaffolds

Abstract

International audienceNovel 3-(2-propynyl)pyrido[2,3-d]pyrimidin-4(3H)-one derivs. and 3-(2-propynyl)quinazolin-4(3H)-one derivs. were prepd. in a high-yielding microwave-assisted one-pot procedure. The one-pot sequence was conveniently extended to the synthesis of com. unavailable 6-bromo-N3-(propargyl)pyrido[2,3-d]pyrimidinone by a regioselective bromination with N-bromosuccinimide (NBS). The synthesis of the target compds. was achieved using 2-aminobenzoic acid and 2-amino-3-pyridinecarboxylic acid as starting materials. The synthetic scaffolds were successfully converted into triazoles by a copper(I)-catalyzed [3+2] cycloaddn. and substituted at the 6-position by Suzuki-Miyaura cross-coupling in high overall yields

Synthesis and antimicrobial activity of novel 1,2,3‐triazole‐conjugates of quinazolin‐4‐ones

“…Optimized preparative procedures for all ω‐azidoalkylphosphonates 11a – j were previously elaborated in our research groups . Synthesis of N 3 ‐propargylquinazolin‐4‐ones 10a and 10b via application of a one‐pot procedure starting from anthranilic acid 12a or its derivative 12b and N , N ‐dimethylformamide dimethylacetate have been already described . Furthermore, Lazrek and co‐workers as well as Scriba described the synthesis of C2‐substituted N 3 ‐propargylquinazolin‐4‐ones in a two‐step procedure, however, formation of N3‐ and O‐substituted products was observed when potassium tert ‐butoxide/potassium carbonate was used for propargylation of the quinazolinone moiety …”

“…[31,32,34,[37][38][39] Synthesis of N 3 -propargylquinazolin-4-ones 10a and 10b via application of a one-pot procedure starting from anthranilic acid 12a or its derivative 12b and N,N-dimethylformamide dimethylacetate have been already described. [40] Furthermore, Lazrek and co-workers as well as Scriba described the synthesis of C2-substituted N 3propargylquinazolin-4-ones in a two-step procedure, however, formation of N3-and O-substituted products was observed when potassium tert-butoxide/potassium carbonate was used for propargylation of the quinazolinone moiety. [41,42] For the purpose of this paper a two-step procedure was applied (Scheme 2).…”

“…3-(Prop-2-yn-1-yl)quinazolin-4(3H)-one 10a [42] From quinazolin-4-one 13a (1.00 g, 6.89 mmol) the 3- 6-Bromo-3-(prop-2-yn-1-yl)quinazolin-4(3H)-one 10b [40] (1.00 mmol) in DMF (2 mL) propargyl amine (1.00 mmol) was added and stirred at 50°C for 3 h. Then the mixture was cooled to room temperature, water (5 mL) was added and the precipitated product was filtered and dried on air to give pure 2-amino-N-(prop-2-yn-1-yl) benzamide 15a,b.…”

Cu/Pd‐Catalyzed C‐2–H Arylation of ­Quinazolin‐4(3H)‐ones with (Hetero)aryl Halides

“…[5] Following our efforts on the functionalization of quinazolin-4(3H)-one derivatives, [6] we intended to enhance the procedure by extending the coupling partners to bromo-and chloro(hetero)aryls.…”

Microwave-Assisted Synthesis of Potential Bioactive Benzo-, Pyrido- or Pyrazino-thieno[3,2-d]pyrimidin-4-amine Analogs of MPC-6827

“…To develop sustainable and convenient multicomponent processes for the synthesis of quinazoline and quinazolinone derivatives [ 17 , 18 , 19 ], our group investigated a novel and efficient two-step synthesis of MPC-6827 [ 20 ]. Indeed, reaction of anthranilonitrile with N , N -dimethylacetamide dimethyl acetal (DMA-DMA) at 115 °C for 2 min gave acetimidamide intermediate in excellent yield (90%).…”