Intramolecular nitrene insertions into aromatic and heteroaromatic rings. Part 9. Synthesis of 2-azidodiphenylmethanes and the kinetics of their thermal decomposition in solution

Jones, Gurnos; Long, Brian D.; Thorne, Melanie P.

doi:10.1039/p29920000903

Cited by 10 publications

(3 citation statements)

References 14 publications

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“…In accordance with the aforementioned general procedure, 2‐azidodiphenylmethane (500 mg, 2.39 mmol) was treated with n ‐BuLi (4.78 mmol) to give o ‐( n ‐butylamino)diphenylmethane [16] ( 22d ) (40 mg, 7%) and 2‐benzylaniline [17] ( 21d ) (315 mg, 72%).…”

Section: Methodsmentioning

confidence: 99%

n‐Butyllithium‐mediated reactions of 1‐(2‐azidoarylmethyl)‐ 1H‐benzotriazoles with alkyl halides

Kim

2009

Journal of Heterocyclic Chem

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Treatment of 1‐(2‐azidoarylmethyl)‐1H‐benzotriazoles (6) with n‐BuLi (2.5 equiv.) in THF at −78°C, followed by an addition of alkyl halides such as allyl, benzyl, and ethyl bromides with stirring for 2 h at room temperature afforded 2‐(dialkylamino)‐3‐(benzotriazol‐1‐yl)‐2H‐indazoles (8), 3‐(benzotriazol‐ 1‐yl)‐2H‐indazoles (9), 2‐[(benzotriazol‐1‐yl)methyl]arylamine (10), and 2‐[(benzotriazol‐1‐yl)(alkyl) methyl]arylamine (11). J. Heterocyclic Chem., 2010.

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Section: Methodsmentioning

confidence: 99%

n‐Butyllithium‐mediated reactions of 1‐(2‐azidoarylmethyl)‐ 1H‐benzotriazoles with alkyl halides

Kim

2009

Journal of Heterocyclic Chem

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“…2-Methoxy-5,6-dihydro-11 H -dibenz[ b , e ]azepin-6-one (40). To 2.85 g (13.36 mmol) of 2 amino-5-methoxydiphenylmethane in 26 mL dioxane was added dropwise 0.80 mL (6.68 mmol) of trichloromethyl chloroformate and the mixture was heated at 54 °C (oil bath) for 3 h. Dioxane was removed in vacuo to give a residue of 3.21 g which was Kugelrohr distilled to give the isocyanate as an oil: 2.66 g (83% yield); bp 106−116 °C (air bath temperature) at 4−8 mTorr; TLC analysis (1:10 ether:hexane) indicated a single component at R f 0.54; IR max (film) 2250(s) cm -1 .…”

Section: Methodsmentioning

confidence: 99%

Behavioral Approach to Nondyskinetic Dopamine Antagonists: Identification of Seroquel

et al. 2001

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A great need exists for antipsychotic drugs which will not induce extrapyramidal symptoms (EPS) and tardive dyskinesias (TDs). These side effects are deemed to be a consequence of nonselective blockade of nigrostriatal and mesolimbic dopamine D2 receptors. Nondyskinetic clozapine (1) is a low-potency D2 dopamine receptor antagonist which appears to act selectively in the mesolimbic area. In this work dopamine antagonism was assessed in two mouse behavioral assays: antagonism of apomorphine-induced climbing and antagonism of apomorphine-induced disruption of swimming. The potential for the liability of dyskinesias was determined in haloperidol-sensitized Cebus monkeys. Initial examination of a few close cogeners of 1 enhanced confidence in the Cebus model as a predictor of dyskinetic potential. Considering dibenzazepines, 2 was not dyskinetic whereas 2a was dyskinetic. Among dibenzodiazepines, 1 did not induce dyskinesias whereas its N-2-(2-hydroxyethoxy)ethyl analogue 3 was dyskinetic. The emergence of such distinctions presented an opportunity. Thus, aromatic and N-substituted analogues of 6-(piperazin-1-yl)-11H-dibenz[b,e]azepines and 11-(piperazin-1-yl)dibenzo[b,f][1,4]thiazepines and -oxazepines were prepared and evaluated. 11-(4-[2-(2-Hydroxyethoxy)ethyl]piperazin-1-yl)dibenzo[b,f][1,4]thiazepine (23) was found to be an apomorphine antagonist comparable to clozapine. It was essentially nondyskinetic in the Cebus model. With 23 as a platform, a number of N-substituted analogues were found to be good apomorphine antagonists but all were dyskinetic.

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“…2-Amino-2-methoxybiphenyl 3 d ( R = O C H 3 ) [14], 2-aminodiphenylmethane 5 a ( X = C H 2 ) [15] and 2-aminobenzhydrol 5 c (X=CHOH) [16] were prepared according to literature. Other starting materials 3 a (R=H), 5 b (X=CO), 5 d (X=NH), 5e (X=O) are commercially available.…”

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confidence: 99%

Synthesis of carbazole, acridine, phenazine, 4H‐benzo[def]carbazole and their derivatives by thermal cyclization reaction of aromatic amines

Horaguchi¹,

Oyanagi²,

Creencia³

et al. 2004

Journal of Heterocyclic Chem

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A variety of nitrogen-containing heterocycles were synthesized by passing vapors of aromatic amines over calcium oxide at 450-650 °C under nitrogen carrier gas. Reaction of 2-aminobiphenyl 3 a at 560 °C gave carbazole 4 in 80% yield. Reaction of 2,2'-diaminobiphenyl 3 b a fforded a mixture of carbazole 4 a n d 4-aminocarbozole 6 b. In the case of 2-amino-2'-nitrobiphenyl 3 c, benzo[c]cinnoline 7 was obtained along with carbazole 4. Reaction of 2-amino-2'-methoxybiphenyl 3 d gave four products of carbazole 4, 4-hydroxycarbazole 6 e, phenanthridine 8 and dibenzofuran 9. Reaction of 2-aminodiphenylmethane 5 a a fforded acridine 1 0. In the case of 2-aminobenzophenone 5 b, acridone 11 was obtained as a major product. Reaction of 2-aminobenzhydrol 5 c gave acridine 1 0. When 2-aminodiphenylamine 5 d was reacted, phenazine 1 2 w a s obtained in good yield. In contrast, reaction of 2-aminodiphenyl ether 5 e produced only 2-hydroxydiphenylamine 1 3. Reaction of 4-aminophenanthrene 1 4 produced 4H-b e n z o [d e f]carbazole 1 5 in 61% yield.

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Intramolecular nitrene insertions into aromatic and heteroaromatic rings. Part 9. Synthesis of 2-azidodiphenylmethanes and the kinetics of their thermal decomposition in solution

Cited by 10 publications

References 14 publications

n‐Butyllithium‐mediated reactions of 1‐(2‐azidoarylmethyl)‐ 1H‐benzotriazoles with alkyl halides

n‐Butyllithium‐mediated reactions of 1‐(2‐azidoarylmethyl)‐ 1H‐benzotriazoles with alkyl halides

Behavioral Approach to Nondyskinetic Dopamine Antagonists: Identification of Seroquel

Synthesis of carbazole, acridine, phenazine, 4H‐benzo[def]carbazole and their derivatives by thermal cyclization reaction of aromatic amines

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