440359-60-4

Upstream product

• 1095280-73-1 N-Boc-N-(3-methylphenyl)-O-(4-nitrobenzoyl)hydroxylamine 
• 440359-58-0 2-ethoxycarbonyloxy-3-methoxycarbonylaminotoluene 
• 83-40-9 3-methylsalicylic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 40925-60-8 2,3-dihydro-7-methyl-3H-benzoxazole-2-one 
• 440359-59-1 3-t-butyloxycarbonyl-2,3-dihydro-7-methyl-3H-benzoxazole-2-one 

Downstream Products

• 440359-53-5 2-bromo-N-(2-hydroxy-3-methylphenyl)-5-methyl-3-thiophenecarboxamide 
• 78886-51-8 2-methyl-6-aminophenol hydrochloride 

Relevant academic research and scientific papers

Rearrangement of differentially protected N-arylhydroxylamines

The rearrangement of a series of N,O-difunctionalised N-arylhydroxylamines to generate protected 2-aminophenols has been investigated. N-Boc-N-Aryl-O- acylhydroxylamines are stable, isolable compounds which rearrange smoothly at temperatures between 110 and 140°C. The corresponding N-Boc-N-aryl-O- sulfonylhydroxylamines were not isolated and rearrange to 1,2-difunctionalised aminophenols at room temperature in excellent yield. Deprotection of either the N- or O-substituents under standard conditions allows for further synthetic manipulation of either the aniline or phenol functionality. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Synthesis of thieno[2,3-b][1,5]benzoxazepine derivatives

A new series of 4-(4-methylpiperazin-1-yl)thieno[2,3-b][1,5]benzoxazepines 1a-k has been synthesized from 4-bromo-2-methylthiophene 6 or ethyl 2-amino-4,5-dimethyl-3-thiophencarboxylate 10. Preparation of the key intermediate thieno[2,3-b][1,5]benzoxazepine-4(5H)-ones 4a-i, 4k were carried out by treatment of 2-bromo-N-(2-hydroxyphenyl)-3-thiophencarboxamides 5a-i, 5k with potassium carbonate in DMSO. Compounds 1 are thienoanalogues of loxapine, a potent antipsychotic drug. Of these compounds, the neuroleptic activity of 2-methyl-4-(4-methylpiperazin-1-yl)thieno[2,3-b][1,5]benzoxazepine 1a (R1, R3=H, R2=CH3) demonstrated potent antipsychotic activity.