125701-63-5Relevant academic research and scientific papers
I2/TBHP promoted isocyanide insertion cyclization reaction for the synthesis of quinazolin fused benzoimidazole as a selective methanol detection probe
Ahmadi, Fereshteh,Ahmadi, Nafiseh,Balmohammadi, Yaser,Bazgir, Ayoob,Naimi-Jamal, Mohammad Reza
, (2021)
An efficient I2/TBHP promoted isocyanide insertion cyclization reaction for the synthesis of quinazolines-fused benzoimidazole was reported. The synthesized compounds have a unique potential to use as a selective solvatochromic fluorescence pro
Nickel-Catalyzed Aerobic Oxidative Isocyanide Insertion: Access to Benzimidazoquinazoline Derivatives via a Sequential Double Annulation Cascade (SDAC) Strategy
Shinde, Anand H.,Arepally, Sagar,Baravkar, Mayur D.,Sharada, Duddu S.
, p. 331 - 342 (2017/04/26)
An efficient protocol for the synthesis of quinazoline derivatives through nickel-catalyzed ligand-/base-free oxidative isocyanide insertion under aerobic conditions with intramolecular bis-amine nucleophiles has been developed. A one-pot sequential double annulation cascade (SDAC) strategy involving an opening of isatoic anhydride and annulation to benzimidazole and further nickel-catalyzed intramolecular isocyanide insertion has also been demonstrated. The method is operationally simple to implement with a wide variety of substrates and represents a new approach for multiple C-N bond formations. The methodology has been successfully applied to the syntheses of hitherto unreported imidazo-fused benzimidazoquinazolines via a deprotection-GBB reaction sequence. Further, a florescence study reveals the potential of the present strategy for the discovery of highly fluorescent probes.
Synthesis of benzoimidazoquinazolines by cobalt-catalyzed isocyanide insertion-cyclization
Ahmadi, Fereshteh,Bazgir, Ayoob
, p. 61955 - 61958 (2016/07/11)
An efficient and practical protocol for the synthesis of benzoimidazoquinazoline amines in moderate to good yields by the reaction of isocyanides and benzo[d]imidazol-anilines via a cobalt-catalyzed isocyanide insertion cyclization reaction into the two N
NEW METHODOLOGY FOR THE PREPARATIONOF QUINAZOLINE DERIVATIVES VIA TANDEM AZA-WITTIG/HETEROCUMULENE-MEDIATED ANNULATION. SYNTHESIS OF 4(3H)QUINAZOLINONES, BENZIMIDAZOQUINAZOLINES, QUINAZOLINOQUINAZOLINES AND BENZOTHIAZOLOQUINAZOLINES.
Molina, Pedro,Alajarin, Mateo,Vidal, Angel
, p. 4263 - 4286 (2007/10/02)
The aza-Wittig reaction of iminophosphoranes derived from N-substituted o-azidobenzamides, 2-(o-azidophenyl)-benzimidazole, -benzothiazole or -3,1-benzoxazin-4-one with heterocumulenes leads to functionalized quinazolines.Iminophosphoranes 9, derived from N-substituted o-azidobenzamides, react under mild conditions with isocyanates to form 4H-3,1-benzoxazine-4-imines 11 which are converted into 2-substituted-4(3H)-quinazolinones 12.Iminophosphoranes 9 also react with carbon disulfide and carbon dioxide to give the quinazolinones 13 and 14 respectively.Iminophosphorane 26, derived from 2-(o-azidophenyl)benzimidazole, reacts with isocyanates, carbon disulfide and carbon dioxide to form 6-substituted benzimidazoquinazolines 27, 28, and 29 respectively.In benzene at room temperature, iminophosphorane 31, reacts with isocyanates yielding quinazolinoquinazolines 34.Compounds 34 can also be prepared from iminophosphorane 36 and isocyanates.Iminophosphorane 40 derived from 2-(o-azidophenyl)benzothiazole reacts with aliphatic and aromatic isocyanates or isothiocyanates to give 7H-benzothiazoloquinazoline-7-imines 42.Iminophosphorane 40 also reacts with carbon dioxide or carbon disulfide to afford the corresponding isocyanate 43 or isothiocyanate 44, The molecular structures of 11d and 42a have been determined by X-ray diffraction methods.
