40358-30-3Relevant academic research and scientific papers
Solvent-free synthesis of 1,5-benzothiazepines and benzodiazepines on inorganic supports
Kodomari, Mitsuo,Noguchi, Tomohiro,Aoyama, Tadashi
, p. 1783 - 1790 (2004)
1,5-Benzothiazepines and 1,5-benzodiazepines have been synthesized in solvent-free conditions from chalcones and o-aminothiophenol or o-phenylenediamine in the presence of inorganic support. Silica gel was found to be an effective support for the synthesi
Chalcone-inspired rA1/A2A adenosine receptor ligands: Ring closure as an alternative to a reactive substructure
Aucamp, Janine,Janse van Rensburg, Helena D.,Legoabe, Lesetja J.,Matthee, Chrisna,Terre’Blanche, Gisella
, (2021/12/30)
Over the past few years, great progress has been made in the development of high-affinity adenosine A1 and/or A2A receptor antagonists—promising agents for the potential treatment of Parkinson's disease. Unfortunately, many of these compounds raise structure-related concerns. The present study investigated the effect of ring closures on the rA1/A2A affinity of compounds containing a highly reactive α,β-unsaturated carbonyl system, hence providing insight into the potential of heterocycles to address these concerns. A total of 12 heterocyclic compounds were synthesised and evaluated in silico and in vitro. The test compounds performed well upon qualitative assessment of drug-likeness and were generally found to be free from potentially problematic fragments. Most also showed low/weak cytotoxicity. Results from radioligand binding experiments confirm that heterocycles (particularly 2-substituted 3-cyanopyridines) can replace the promiscuous α,β-unsaturated ketone functional group without compromising A1/A2A affinity. Structure–activity relationships highlighted the importance of hydrogen bonds in binding to the receptors of interest. Compounds 3c (rA1Ki?=?16?nM; rA2AKi?=?65?nM) and 8a (rA1Ki?=?102?nM; rA2AKi?=?37?nM), which both act as A1 antagonists, showed significant dual A1/A2A affinity and may, therefore, inspire further investigation into heterocycles as potentially safe and potent adenosine receptor antagonists.
Graphite oxide: A metal free highly efficient carbocatalyst for the synthesis of 1,5-benzodiazepines under room temperature and solvent free heating conditions
Jamatia, Ramen,Gupta, Ajay,Dam, Binoyargha,Saha, Mithu,Pal, Amarta Kumar
supporting information, p. 1576 - 1585 (2017/05/10)
Graphite Oxide (GO), an attractive metal free carbocatalyst, was employed as a green and highly efficient catalytic system for the synthesis of 1,5-benzodiazepines. The reaction was studied at room temperature as well as at 80°C under solvent free heating
Construction of the 1,5-Benzodiazepine Skeleton from o-Phenylendiamine and Propargylic Alcohols via a Domino Gold-Catalyzed Hydroamination/Cyclization Process
Cacchi, Sandro,Fabrizi, Giancarlo,Goggiamani, Antonella,Iazzetti, Antonia
supporting information, p. 3511 - 3513 (2016/08/16)
The gold-catalyzed reaction of o-phenylendiamine with propargylic alcohols affords 1,5-benzodiazepines bearing different substituents on the 2 and 4 positions. The method allows even for the selective preparation of 4-substituted 1,5-benzodiazepine derivatives.
Solvent free oxalic acid catalyzed synthesis of 1,5-benzodiazepines
Sarkate, Aniket P.,Sangshetti, Jaiprakash N.,Dharbale, Nanasaheb B.,Sarkate, Ajinkya P.,Wakte, Pravin S.,Shinde, Devanand B.
, p. 2200 - 2203 (2014/03/21)
In the present study 1, 5-benzodiazepines were synthesized from a range of α β-unsaturated ketones and o-phenylendiamine using oxalic acid 10 mol% as a catalyst under solvent free conditions. The yields of the present method are better than the reported method which explains effectiveness of oxalic acid catalyst. The cost effective, resourceful, undemanding and environment friendly are the advantageous aspects of this method.
1,5-Benzoheteroazepines through eco-friendly general condensation reactions
Nardi, Monica,Cozza, Annalisa,Maiuolo, Loredana,Oliverio, Manuela,Procopio, Antonio
experimental part, p. 4827 - 4834 (2011/10/04)
Condensation reactions of o-phenylenediamine and 2 equiv of acetone produce biaryl-substituted 1,5-benzodiazepines. The synthetic protocol shows general applicability since similar reaction of o-phenylenediamines, o-aminophenol, and o-aminothiophenol with
New access to the one-pot solvent-free synthesis of 4,5-dihydro-pyrido[2,3- b][1,4]diazepines and 2,3-dihydrobenzo[b][1,4]diazepines by microwave irradiation
Goswami, Shyamaprosad,Hazra, Anita,Jana, Subrata
experimental part, p. 861 - 865 (2009/12/24)
(Chemical Equation Presented) A series of diversely substituted pyridodiazepines and benzodiazepines have been synthesized in solvent and catalyst free microwave condition from aryl/heteroaryl diamines and b-aryl vinyl ketones. The yields of the reactions
A new and efficient one-pot solid-supported synthesis of 1,2,4,6-tetraaryl-1,4-dihydropyridines
Verma, Anil K.,Koul, Summon,Razdan, Tej K.,Kapoor, Kamal K.
, p. 1064 - 1073 (2007/10/03)
1,2,4,6-Tetraaryl-1,4-dihydropyridines were obtained by the one-pot reaction of chalcones and substituted anilines on the surface of Bi(III)nitrate-Al2O3. The reaction seems to proceed via β-oxygenation of Bi(III) enolised chalcones followed by Michael addition and heteroannulation with simultaneous retro aldol disproportionation. The presence of the ring-activating groups at ortho and para positions in the aniline seems to be essential for the reaction.
SbCl3-Al2O3-catalyzed, solvent-free, one-pot synthesis of benzo[b]1,4-diazepines
Ganai, Bilal A.,Kumar, Satish,Andotra, Charanjeet S.,Kapoor, Kamal K.
, p. 803 - 807 (2007/10/03)
This article explores the use of antimony(III) chloride adsorbed on neutral alumina as an efficient catalyst for the one-pot synthesis of benzo[b]1,4-diazepines (83-94%) under solvent-free conditions. The process is easy, efficient, ecofriendly, and econo
Protic acidic ionic liquids promoted formation of 1,5-benzodiazepines: Remarkable effects of cations and anions on their performances
Du, Yuying,Tian, Fuli
, p. 486 - 489 (2007/10/03)
A series of protic acidic ionic liquids have been used as solvents and catalysts for the synthesis of 1,5-benzodiazepines. Success of the condensation appears to lie in the choice of cation-anion combinations and the ionic liquid [HBIm]CF3SOsu
