Facile One-Pot Assembly of Imidazotriazolobenzodiazepines via Indium(III)-Catalyzed Multicomponent Reactions

Abstract

An operationally simple, one-pot multicomponent reaction has been developed for the assembly of 9H-benzo[f]imidazo[1,2-d][1,2,3]triazolo[1,5-a][1,4]diazepines adorned with three diversification points via an atom-economical transformation incorporating α-diketones, o-azidobenzaldehydes, propargylic amines, and ammonium acetate. This process involves tandem InCl3-catalyzed cyclocondensation and intramolecular azide-alkyne 1,3-dipolar cycloaddition reactions; optimization data, substrate scope, and mechanistic insights are discussed.

Rapid assembly of heterocycle grafted macrocycles via tandem one-pot double 1,3-dipolar cycloaddition reaction

“…In the IR spectrum of 10a, the two carbonyl groups showed peaks at 1720 and 1612 cm −1 . The H a proton resonated as a doublet at δ 3.87 (d,J = 7.2 Hz). A multiplet in the region of δ 2.95-2.99 was observed for the H b proton.…”

“…The organic layer was dried (Na 2 SO 4 ) and evaporated under reduced pressure and the residue was chromatographed over SiO 2 using hexane-ethyl acetate (4 : 1) as the Scheme 7 Tandem one-pot 1,3-DC reaction. (d,J = 3 Hz,1H); 4.63 (d,J = 3.6 Hz,1H); 4.91 (d,J = 3.6 Hz,1H); 5.94 (d,J = 3.9 Hz,1H);6.96 (dd,J = 3.9,15.3 Hz,1H);7.16 (dd,J = 1.8,15.3 Hz,1H);2H);7.85 (d,J = 8.7 Hz,2H). 13 C NMR (75 MHz,CDCl 3 ): 25.2,25.8,56.7,74.6,77.6,78.6,81.4,81.5,103.8,111.1,125.2,127.8,129.1,134.7,138.3,140.3,187.6 5 mmol).…”

“…The crude product was purified by column chromatography using hexane-EtOAc (7 : 3) 7, 24.1, 24.7, 25.3, 39.2, 46.7, 59.2, 62.3, 66.5, 77.5, 81.2, 81.5, 103.5, 108.5, 110.6, 116.1, 121.3, 122.5, 124.1, 136.9, 140.1, 148.6, 157.1, 164.9, 180. 1 Hz,1H);7.03 (t,J = 7.5 Hz,1H);7.16 (dd,J = 1.8,15.6 Hz,1H);4H);7.66 (s,1H);7.90 (d,J = 8.7 Hz,2H). 13 C NMR (75 MHz,CDCl 3 ): 23.9,24.5,38.4,45.9,61.6,77.1,80.5,80.6,102.7,107.1,109.9,115.3,121.6,122.4,123.0,123.2,126.7,127.9,133.0,135.9,137.5,139.8,142.6,147.9,156.3,179.9,186.4 (d,J = 3 Hz,1H); 4.10 (q, J = 7.2 Hz, 2H); 4. 50-4.63 (m, 3H); 4.67-4.70 (m, 1H); 4.85 (s, 2H); 5.43 (d,J = 1.8 Hz,2H); 5.86 (d,J = 3.6 Hz,1H);…”

“…13 C NMR (75 MHz,CDCl 3 ): 23.9,24.5,38.4,45.9,61.6,77.1,80.5,80.6,102.7,107.1,109.9,115.3,121.6,122.4,123.0,123.2,126.7,127.9,133.0,135.9,137.5,139.8,142.6,147.9,156.3,179.9,186.4 (d,J = 3 Hz,1H); 4.10 (q, J = 7.2 Hz, 2H); 4. 50-4.63 (m, 3H); 4.67-4.70 (m, 1H); 4.85 (s, 2H); 5.43 (d,J = 1.8 Hz,2H); 5.86 (d,J = 3.6 Hz,1H);6.03 (dd,J = 1.5,15.9 Hz,1H);2H);7.03 (t,J = 7.5 Hz,1H);2H);2H);7.40 (s,1H);1H);7.54 (d,J = 7.2 Hz,1H). 13 C NMR (75 MHz,CDCl 3 ): 14.2,26.1,26.7,43.6,53.6,…”

“…50-4.63 (m, 3H); 4.67-4.70 (m, 1H); 4.85 (s, 2H); 5.43 (d,J = 1.8 Hz,2H); 5.86 (d,J = 3.6 Hz,1H);6.03 (dd,J = 1.5,15.9 Hz,1H);2H);7.03 (t,J = 7.5 Hz,1H);2H);2H);7.40 (s,1H);1H);7.54 (d,J = 7.2 Hz,1H). 13 C NMR (75 MHz,CDCl 3 ): 14.2,26.1,26.7,43.6,53.6,60.4,64.0,79.2,82.7,83.4,104.9,110.8,112.0,117.6,122.8,123.3,124.0,125.5,128.1,128.7,134.6,135.2,138.4,141.2,144.9,150.4,158.2,166.0,183.0 (d,J = 3 Hz,1H); 4.52 (d,J = 12.6 Hz,1H); 4.62 (d,…”