Solid-phase synthesis of isoalloxazines using merrifield resin

Abstract

A reação da resina de Merrifield ligada a compostos diamino com aloxan monohidrato, resultou em uma resina ligada a isoaloxazinas 10-substituídas, que foram caracterizadas por fluorescência em fase sólida e espectroscopia de IV. A resina foi segmentada por solução aquosa de HF/DMF a 40%, obtendo-se isoaloxazinas 7-carboxi-10-substituídas, que foram caracterizadas por UV-Vis., IV, 1 H RMN, fluorescência e análise elementar.The reaction of Merrifield resin bound diamino compounds with alloxan monohydrate gave 7-resin bound 10-substituted isoalloxazines that were characterized by solid phase fluorescence and IR spectroscopy. The resin was cleaved by 40% aqueous HF/DMF to give 7-carboxy-10-substituted isoalloxazines that were characterized by UV-vis., IR, 1 H NMR, fluorescence and elemental analysis.

Application of Resin-Bound Reagents for the Synthesis of Benzimidazole Derivatives

“…of Cl per g) 1 with sodium 4-chloro-3-nitrobenzoate 2. 32 The reaction of resin 3 with different substituted anilines was carried out in N,N-dimethylformamide (DMF) to obtain the desired resin-bound 4-(N-substituted amino)-3-nitrobenzoates 4a-d. 32,33 The reduction of 4a-d with tin(II) chloride 32,33 afforded the resin-bound key compounds 4-(N-substituted amino)-3-aminobenzoates 5a-d.…”

“…The cyclocondensation of resins 5a-d with the sodium bisulfite adducts of aromatic aldehydes 34,35 gave resinbound 1,2-disubstituted benzimidazoles 6a-g, which, upon cleavage with hydrofluoric acid (HF) in DMF, 32 In an efficient exploitation of solid-phase chemistry, this work describes the preparation of the new resin-bound 4-(N-arylamino)-3-aminobenzoates and their successful cyclocondensations with the sodium bisulfite adducts of different aldehydes and triethyl orthoformate or triethyl orthoacetate, followed by resin cleavage to produce the target 1,2-diaryl-and 1-aryl-2-(un)substituted benzimidazole-5-carboxylic acid derivatives, respectively. In another variation, the cyclocondensation of the resin-bound 4-(N-arylamino)-3-aminobenzoates with carbon disulfide afforded the corresponding resin-bound thioxobenzimidazoles, which upon cleavage gave the corresponding 2-thioxobenzimidazoles.…”

Role of Interfacial Tension of Solvating Diluents and Hydrophilic–Hydrophobic Cross-Linkers in Hyper-Cross-Linked Solid Supports

“…Over the decade, polymers have been extensively used in different fields due to their enormous potential applications. − Mostly, beaded microspheres were used in solid-phase synthesis as a support for substrate, reagent, catalyst, protecting group, enzyme immobilization, etc. In industry, it is economical to use polymer-supported compounds due to their easy recovery, recycle, and reuse.…”