112253-72-2Relevant articles and documents
Novel substituted triazolo benzodiazepine scaffolds to explore chemical space
Abeykoon, Gayan A.,Sahn, James J.,Martin, Stephen F.
, (2021/02/16)
Efficient and concise routes to sets of novel triazolo-1,4-benzodiazepine scaffolds that are suitably functionalized for diversification at three positions to explore three-dimensional space with different substituents are described. One approach to these scaffolds features a simplified multicomponent assembly process to give an intermediate azido alkyne that undergoes a facile Huisgen dipolar cycloaddition. The triazolo-1,4-benzodiazepines thus produced may be endowed with aryl halide, secondary amino, alcohol, aldehyde or carboxylic acid groups as functional handles for orthogonal derivatization reactions. Modification of this approach enabled the facile synthesis of the related triazolo-1,4-benzodiazepin-6-ones, also bearing three functional handles. These convenient protocols were used to prepare multi-gram quantities of benzodiazepine analogs as precursors for generating compound libraries for screening campaigns.
Synthesis of 2,1-benzisoxazole-3(1H)-ones by base-mediated photochemical N-O bond-forming cyclization of 2-azidobenzoic acids
Dzhons, Daria Yu.,Budruev, Andrei V.
supporting information, p. 874 - 881 (2016/07/06)
The base-mediated photochemical cyclization of 2-azidobenzoic acids with the formation of 2,1-benzisoxazole-3(1H)-ones is reported. The optimization and scope of this cyclization reaction is discussed. It is shown that an essential step of the ring closure of 2-azidobenzoic acids is the formation and photolysis of 2-azidobenzoate anions.
Intramolecular 1,3-Dipolar Cycloadditions. Part 1. A Facile Synthesis of Benzimidazo- and Quinazolinotriazolobenzodiazepines
Mohiuddin, Ghulam,Reddy, Padala Satyanarayana,Ahmed, Khalil,Ratnam, Chengalvala Venkata
, p. 1839 - 1868 (2007/10/02)
The synthesis of hitherto unknown 9H-benzimidazotriazolobenzodiazepines (4, 11a-e and 12a-c) and 9H-quinazolinotriazolobenzodiazepin-11-ones (5 and 18a-g) is reported. 2-(2-Azidoaryl)benzimidazoles (6 and 10a-h) and 2-(2-azidoaryl)quinazolin-4(3H)-ones (7 and 17a-g) react with propargyl bromide to give non-isolable intermediates which undergo an intramolecular 1,3-dipolar cycloaddition to the title compounds.