102771-27-7

Basic information

• Product Name: 5-(4-nitrophenyl)-8-methyl-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepine
• Synonyms: 5-(4-nitrophenyl)-8-methyl-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepine
• CAS NO: 102771-27-7
• Molecular Weight: 323.308
• Mol File: 102771-27-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 5-(4-nitrophenyl)-8-methyl-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-nitrophenyl)-8-methyl-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepine(102771-27-7)
• EPA Substance Registry System: 5-(4-nitrophenyl)-8-methyl-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepine(102771-27-7)

Safety Data

• Hazardous Substances Data: 102771-27-7(Hazardous Substances Data)

Upstream product

• 717903-52-1 6-(trimethylsilyl)benzo[d][1,3]dioxol-5-yl triflate 
• 433716-67-7 2-(4-nitrobenzoyl)-4,5-methylenedioxyphenylacetone 
• 4676-39-5 1-(1,3-benzodioxol-5-yl)-2-propanone 
• 6974-61-4 β-oxy-α-(3',4'-methylenedioxyphenyl)propane 
• 94-59-7 1-allyl-3,4-methylenedioxybenzene 

Downstream Products

• 102771-26-6 1-(4-aminophenyl)-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine 
• 220669-84-1 8-methyl-7-methylcarbamoyl-5-(4-nitrophenyl)-7H-1,3-dioxolo-/4,5-h//2,3/benzodiazepine 
• 143692-49-3 1-(4-Nitrophenyl)-4-methyl-7,8-methylenedioxy-3,4-dihydro-5H-2,3-benzodiazepine 
• 114460-08-1 GYKI 52895 
• 194729-02-7 [5-(4-nitro-phenyl)-9H-1,3-dioxa-6,7-diaza-cyclohepta[f]inden-8-ylmethylene]-hydrazine 
• 194729-03-8 C₁₇H₁₁N₅O₄ 
• 194728-85-3 8-formyl-5-(4-nitrophenyl)-9H-1,3-dioxolo (4,5-h)(2,3)benzodiazepine 

Relevant articles and documents

Synthesis of 2,3-benzodiazepines and 2,3-benzodiazepin-4-ones from arynes and β-diketones

2,3-Benzodiazepines were synthesized by two-step or one-pot reactions from aryne precursors. Reaction of 2- (trimethylsilyl)aryl triflates with β-diketones in the presence of CsF gave ortho-substituted benzophenones. Treatment of benzophenones with hydrazine hydrate resulted in the formation of 2,3-benzodiazepines in moderate yields. Tofisopam, a well known anxiolytic, could be synthesized via C-C bond insertion of 3,4-dimethoxybenzyne with 2-ethyl-1-(3,4-dimethoxyphenyl)butane-1,3-dione, followed by the reaction with hydrazine hydrate in one-pot operation. 2,3-Benzodiazepin-4-ones were also synthesized by the reaction of β-keto esters with triflates in the presence of CsF, followed by the addition of hydrazine hydrate. Substituted isoquinolines were synthesized by the reaction of ortho-substituted benzophenones with ammonium hydroxide.

A simple and efficient synthesis of GYKI 52466 and GYKI 52895

The synthesis of 1-(4-aminophenyl)-4-methyl-7,8-methylene-dioxy-5H-2,3-benzodiazepine (GYKI 52466, 1), the prototype of a series of noncompetitive AMPA receptor antagonists, and its 3,4-dihydroderivative (GYKI 52895, 2) is described. The title compounds have been prepared starting from safrole through a quite effective procedure.