1,2-Dianilino

Aufahnlichem Wege(Natronlauge Glykol 140° 2 h) erhalt man 3,4-Dianilino-furazan(R = nh-c6hs 37% Schmp. 221-2220)66. 

Smolinsky and Feuer have observed that treatment of 2-phenyl-1-azirine with aniline followed by mild acid hydrolysis gives mainly benzanilide, in addition to smaller amounts of 2,5-diphenylpyrazine and 3,4-dianilino-l, 2,5-triphenylpyrrole.86 These products have been rationalized as initially proceeding by nucleophilic attack of the amine at the imine carbon atom to give intermediate 154. No effort to isolate the 2-phenyl-2-anilinoaziridine (155) or (156) was made. 

Acetone also reacts with diphenylamine, in the presence of acid, to form a variety of condition-dependent products (5). Excess amine and a small amount of strong acid catalyst at 100—150°C give 2,2-[4,4 -(dianilino)diphenyl]-propane [2980-26-9] (6). With a large amount of hydrochloric acid at 250°C in the presence of excess diphenylamine, the main product is 9,9-dimethylacridan [6267-02-3]. 

Hydrolyses of aminopyridopyrimidines to the corresponding pyridopyrimidones by means of acid, base, and nitrous acid have been reported. 4-Amino compounds are stable to nitrous acid, but are much more labile than the 2-amino derivatives toward acid- or base-catalyzed hydrolysis. The aminochloro-pyrido[2,3-d]pyrimidine (160) has been converted into the 2,4-dianilino analog (161) by reaction with aniline." ... 

Bis(substituted amino)-4,8-bisethylthio (or carboxymethylthio)-pyrimido[5,4-d]pyrimidines (464) are aminated first at the 4-position with primary or secondary amines at 180° (2 hr) and then at the 8-position (200°, 4 hr). The 4,8-bisthioxo derivative of 464 is 4,8-diaminated with ethanolamine (170°, 1 hr). 2,6-Dianilino-4,8-dioxo(or diethoxy or dibenzyloxy) derivatives of 464 react at the 4-and 8-positions with primary or secondary amines at 180°. The 2,4,6,8-tetrachloro derivative is claimed to goto the tetrakis(triethylammonio) compound. ... 

The DuPont company used the succinic acid ester process, in which diethyl succinate is first cyclised to diethyl succinylsuccinate (2.39) in a sodium/alcohol mixture. One mole of the product is next condensed with two moles of aniline under oxidising conditions, forming diethyl 2,5-dianilino-3,6-dihydroterephthalate (2.40). Ring closure at 250 °C gives dihydroquinacridone, from which quinacridone is obtained by oxidising away the two extra hydrogen atoms. 

Succinylosuccinic dialkylester is treated with two equivalents of aniline to yield the 2,5-dianilino-3,6-dihydroterephthalic dialkylester 55. Without separating the intermediate, the ring is closed thermally (at 250°C) in the same reaction medium to afford the a-modification of dihydroquinacridone 56 [4, 6] ... 

The great affinity of quinone for hydrogen leads to the formation of anilinoquinone which can now, in the same way, add a further equivalent of aniline to the half of the molecule not yet involved. The dianilino-quinol is converted into dianilinoquinone in the same way as the first reaction product was changed. (Write the equation.)... 

Hexadien und 1,5-Cyclooctadien reagieren unter sonst gleichen Bedingungen mit 2-Aquivalenten Thallium(III)-acetat und 3-Aquivalentcn Anilin zu 2,5-Bis-[anilinome-thyl]- 1-phenyl-pyrrolidin (75%) bzw. 2,6-Dianilino-9-phenyl-9-aza-bicyclo[3.3.1]-nonan <70%>-... 

Bei der Reduktion von N-Phenyl-iminen mit Zink in siedendem Ethanol/Perchlorsaure (20 1) in Gegenwart von Quecksilber(II)-chlorid3 oder mit Zink in siedendem Ethanol/ Chloroform (20 l)4 erfolgt reduktive C- C-Verknupfung unter Bildung von 1,2-sub-stituierten 1,2-Dianilino-alkanen, wie hier fur die Synthese von 1,2-Bis-[4-dimethyl-amino-phenyl]- , 2-dianilino-ethan gezeigt ... 

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