65441-00-1

Upstream product

• 150-13-0 4-amino-benzoic acid 
• 104-15-4 toluene-4-sulfonic acid 
• 98-59-9 p-toluenesulfonyl chloride 
• 75057-16-8 N-(p-Tolylsulphonyloxy)-1-phenylnaphthalene-2,3-dicarboximide 
• 87813-97-6 Toluene-4-sulfonic acid 1,3-dioxo-1,3,3a,4,7,7a-hexahydro-isoindol-2-yl ester 

Relevant academic research and scientific papers

Single-crystal and molecular structures of six hydrogen-bonding 3D supramolecular salts from 2-aminobenzoic acid, 3-aminobenzoic acid, 4-aminobenzoic acid, and acidic components

Cocrystallization experiments of the commonly available 2-aminobenzoic acid/3-aminobenzoic acid/4-aminobenzoic acid, with a series of organic acids gave a total of six anhydrous molecular salts. The structures of these salts were subsequently characterized by IR, EA, and XRD analysis technique, and the melting points of all salts were also reported. In the six salts, the NH2 of the aminobenzoic acids are protonated when the organic acids are deprotonated, and the crystal packing is interpreted in terms of strong N–H?O H-bonds from the NH3 + and deprotonated acidic groups. Except the N–H?O H-bond, the O–H?O H-bonds were also found at 1–6. The salts of the aryl sulfonates exhibited the N–H?S H-bonds, and salt 4 has the additional O–H?S H-bond. In these structures homo or hetero supramolecular synthons or both were produced, making R1 2(3), R1 2(5), R1 2(7), R2 1(6), R2 2(4), R2 2(5), R2 2(8), R2 2(12), R2 2(16), R2 3(6), R3 2(7), R3 2(9), R3 3(8), R3 3(9), R3 3(10), R4 2(8), R4 2(18), R4 2(14), R4 4(12), R4 4(22), R6 5(18), and R6 6(26) rings which could have important function in the formation and stabilization of the crystals. But not all of them were appeared repeatedly, as most of them occurred only in some structures. Nevertheless R4 2(8), R4 3(10) and R4 4(12) usually observed in organic solids of organic acids with amine, were again shown to be involved in most of these H-bonding networks. Further inspection into the crystal packing of the salts indicated that a large variety of different secondary interactions were also existed in 1–6, which contribute to the stabilization and expansion of the total 3D framework structures.

Imides: Part IV - Synthesis and Reactions of N-(Arylsulphonyloxy)cyclohex-4-ene-1,2-dicarboximides

N-(Arylsulphonyloxy)cyclohex-4-ene-1,2-dicarboximides (IIa and IIb) undergo base-catalysed Lossen rearrangement with aromatic amines in refluxing ethanol to give mixtures of N-(2-arylcarbamoyl)cyclohex-4-enyl-N'-arylureas (IIIa-d) and the amine salts of arylsulphonic acids (IVa-h).Fusion of II with aromatic amines for 15 min gives mixtures of 3-arylquinazoline-2,4-diones (VIa-c) and IV; however fusion for 1 hr affords mixtures of sym-N,N'-diarylureas (VIIa-d) and IV.Compounds IIa and IIb also react with phenylhydrazine to give mixtures of VIII and phenylhydrazine saltof arylsulphonic acids (IXa and IXb).The mass spectra of IIb and IIIa are presented, and discussed.

Synthesis of Benzoquinazoline-2,4-diones via Lossen Rearrangement of N-(Arylsulphonyloxy)naphthalene-2,3-dicarboximide Derivatives

Treatment of N-(arylsulphonyloxy)-1-phenylnaphthalene-2,3-dicarboximides (IIa, b) with ammonia, aromatic amines, amino acids and hydrazine hydrate brings about the imide ring opening followed by Lossen rearrangement to give benzoquinazoline-2,4-diones (IIIa-h) and the salts of arylsulphonic acids (IVa-p).