49604-61-7

Upstream product

• 91-40-7 2-(phenylamino)benzoic acid 
• 593-51-1 methylamine hydrochloride 
• 57623-73-1 2-(phenylamino)benzoyl chloride 
• 74-89-5 methylamine 
• 35708-19-1 Methyl N-phenylanthranilate 

Downstream Products

• 24103-82-0 2-Methylaminomethyl-diphenylamin 
• 100-52-7 benzaldehyde 
• 16285-32-8 2,3-dihydro-3-methyl-2-phenylquinazolin-4(1H)-one 
• 1596243-51-4 1,3-dimethyl-2-phenyl-1,2,3,4-tetrahydroquinazoline 
• 73302-18-8 1-methyl-2,3-diphenyl-2,3-dihydroquinazolin-4(1H)-one 
• 39601-77-9 C₁₅H₁₄N₂S 
• 39601-58-6 N-methyl-2-(phenylamino)benzothioamide 
• 24103-85-3 2-((dimethylamino)methyl)-N-phenylaniline 
• 68615-02-1 3-methyl-2-oxo-1-phenyl-2,3-dihydro-1H-2λ⁵-benzo[1,3,2]diazaphosphinin-4-one 

Relevant academic research and scientific papers

Experimental and theoretical investigations into the stability of cyclic aminals

Background: Cyclic aminals are core features of natural products, drug molecules and important synthetic intermediates. Despite their relevance, systematic investigations into their stability towards hydrolysis depending on the pH value are lacking. Results: A set of cyclic aminals was synthesized and their stability quantified by kinetic measurements. Steric and electronic effects were investigated by choosing appropriate groups. Both molecular mechanics (MM) and density functional theory (DFT) based studies were applied to support and explain the results obtained. Rapid decomposition is observed in acidic aqueous media for all cyclic aminals which occurs as a reversible reaction. Electronic effects do not seem relevant with regard to stability, but the magnitude of the conformational energy of the ring system and pKa values of the N-3 nitrogen atom. Conclusion: Cyclic aminals are stable compounds when not exposed to acidic media and their stability is mainly dependent on the conformational energy of the ring system. Therefore, for the preparation and work-up of these valuable synthetic intermediates and natural products, appropriate conditions have to be chosen and for application as drug molecules their sensitivity towards hydrolysis has to be taken into account.

Organic Synthesis with N-Heterocyclic Carbenes of Indazole: Synthesis of Benzo(thio)imidates, Benzo[d][1,3]thiazines and Quinazoline-4-thiones

The N-heterocyclic carbenes of indazole, generated by deprotonation of indazolium salts, proved to be versatile starting materials for organic synthesis. They undergo ring-opening reactions to generate ketenimines which readily add thiols thus affording what are, to the best of our knowledge, the first examples of 2-anilinobenzothioimidates. Water converts the ring-opened intermediates into functionalized 2-anilinobenzamides which can be thionated with Lawesson's reagent and subsequently cyclized with formaldehyde and propionaldehyde, respectively, to give benzo[d][1,3]thiazines and quinazoline-4-thiones. The outcome of the cyclization depends upon the thiobenzamide substitution pattern.

A Novel Oxamide Rearrangement

An efficient, base-induced rearrangement of 2-benzoic acid methyl ester (7a) to the isomeric 2-benzoic acid methyl ester (27a) is described.This novel rearrangement must proceed through a spiro intermediate wherein benzoate is acting as a Michael receptor.When 2-benzoic acid methyl ester (28) - an oxamide which would produce a degenerate spiro intermediate - was subjected to rearrangement conditions, the product obtained was 1,3-dimethyl-2,4-(1H,3H)quinazolinedione (29).This latter transformation may have proceeded via a benzodiazepinetrione intermediate.