Dibenzo

The solvent was evaporated from the combined benzene extracts to give 33.4 g of a clear light brown resin. Crystallization from an alcohol-water mixture gave 19.5 g of 1-methyl-4-(5-hydroxy-5-dibenzo[a,e] cycloheptatrienyO-piperidine, MP 156° to 157°C. Two recrystallizations from alcohol-water mixtures followed by two recrystallizations from benzene-hexane mixtures gave analytically pure product, MP 166.7° to 167.7°C. 

Cl Preparation of 1 -Methyt-4-(5-Dibenzo[a,e] Cydoheptatrienytidenej-Piperidine Hydrochloride 1-Methyl-4-(5-hydroxy-5-dibenzo[a,e] cycloheptatrienyO-piperidine (3.05 g,... 

Dibenzo[c /][l, 3]diazepines 5 or 6 bearing an amino or substituted amino group in position 6 are obtained from biphenyl-2,2 -diamine and 2-methylisothiourea sulfate or ALAAdiisoprop-ylcarbodiimide, respectively.175... 

The formation of 5//-dibenzo[r/,/][l,3]diazepin-6(7//)-one (13, R = H) in good yield by fusing biphenyl-2,2 -diamine with urea was reported in 1901177 and has since been extended to the preparation of numerous analogs.178 Selected examples are given yields were generally not reported.177-179... 

The sulfur analog, 5//-dibenzo[d,./][1,3]diazcpin-6(7//)-thiotie (14), is formed from biphenyl-2, 2 -diamine and carbon disulfide.175... 

Catalytic hydrogenation of 5//-dibenzo[r/,/][l, 2,3]triazepine gives biphenyl-2-amine (2).331... 

Perkin Trans. 2, 1996, 67 for a related example with 5-ethynyl-5//-dibenzo[a,d]cyclo-hepten-5-ol. 

CN 7-[(10,l 1-dihydro-5//-dibenzo[a4]cyclohepten-5-yl)amino]heptanoic acid... 

CN 3-(5//-dibenzo[a, flcyclohepten-5-ylidene)-WA-dimethyl-I-propanamine hydrochloride... 

CN en io-3-[(10,ll-dihydro-5//-dibenzo[a,d]cyclohepten-5-yl)oxy]-8-methyl-8-azabicyclo[3.2.1]octane citrate (1 1)... 

Brown s result was supported by later experiments in which bromonium ions were generated by bubbling gaseous hydrobromic acid through a solution of bromohydrins in halogenated solvents. Under these conditions, bromine is eliminated as it is formed, so that the resulting alkene is observed directly (Scheme 15). This method has been applied to the bromohydrins derived from cis- and trans-stilbenes (Scheme 16) and from 5//-dibenzo[a,d]-cycloheptene and -azepine systems ([29a] and [29b] respectively Scheme 17), in which steric constraints should favour elimination (path a) as against substitution (path b). 

Oxadiazole-3,4-diamine forms the H-bonded supramolecular monohydrated complex with [1.5]dibenzo-18-crown-6 ([1.5]DB18C6) <2005JPM63>. 

Fig. 10 Structures of dyes (a) 3,3 -di(3-sulfopropyl)-9-amino-thiacarbocyanine (dye 8), (b) 3,3 -di(3-sulfopropyl)-4,5,4, 5 -dibenzo-9-phcnyl-thiacarbocyanine (PTC), (c) meso-tetrakis(p-sulfo-natophenyl) porphine (TSPP, at pH lower than 4.8)...

G. Bellucci, C. Chiappe, F. Marioni, C. Simonelli, The Low Reactivity of 5//-Di bcnzo-[c(,rf]cyclohcplcne 10,11-Oxide in Microsomal Epoxide Hydrolase Catalyzed Hydration , Xenobiotica 1989, 19, 279 - 285 G. Bellucci, G. Berti, C. Chiappe, F. Fabri, F. Marioni, Product Enantioselectivity in the Microsomal Epoxide Hydrolase Catalyzed Hydrolysis of 10,11 -Di hydro-10,11 -epoxy-5//-dibenzo[c ,rf]cyclohcplcnc , J. Org. Chem. 1989, 54, 968 - 970. 

Base used was NaH(l.l equiv). Data from ref 39, 15-Crown-5. Dibenzo-18-Crown-6. PEG = Poly, ... 

More recently, Carreira and coworkers reported the reactions of sulfamic acid with branched allylic alcohols to form branched primary allylic amines [106]. One enantioselective reaction was disclosed, and the product was isolated in 70% ee when using a 5//-dibenzo[h, / jazepine-derived phosphoramidite with [lr(COE)2Cl]2 (Scheme 33). This reaction occurs under acidic conditions, which is incompatible with the metalacyclic catalysts. 

Small changes in the solvent or in the conditions of oxidation can lead to changes in the electronic and molecular structure of aryldiazo radical cations, from a linear allylic 7T- to a bent a-radical state. Both states have been observed in the radical cations of diphenyldiazomethane (49) and 5-diazo-10,ll-dihydro-5//-dibenzo[a, /]cycloheptene... 

Protriptyline Protriptyline, A-methyl-5-//-dibenzo[a,d]cyclohepten-5-propylamine (7.1.22), differs from all of the drugs described above in that there is present a double bond at the Cio-Cji position of the central 7-membered ring of the tricyclic part of the molecule. At the same time, a free electron pair on C, belonging to either a nitrogen atom or an exo-cyclic double bond are excluded, which undoubtedly changes both the architecture of the whole molecule as well as, the collocation of pharmacophore groups. 

Cyclobenzaprine Cyclobenzaprine, A,lV-dimethyl-3 -(dibenzo[a,d]cyclohepten-5-ylidene) propylamine (15.3.9), is synthesized by reacting 5//-dibenzo[a,d]cyclohepten-5-one with 3-dimethylaminopropyhnagnesium chloride and subsequent dehydration of the resulting carbinol (15.3.8) in acidic conditions into cyclobenzaprine (15.3.9) [30-32]. 

A poly (vinylchloride) membrane electrode was described for local anesthetics, based on dibenzo-24-crown-8 as the electroactive material, and di(2-ethyl)hexyl phthalate as the plasticizer [74]. It was reported that the electrode exhibited a Nemstian response to procaine, and other electrode properties were also presented. The analysis was performed at pH 6 to 6.5 vs. S.C.E., with a 0.2 M lithium acetate agar bridge. Less efficient crown ethers studied at this time were benzo-15-crown-5, dibenzo-18-crown-6, and dibenzo-30-crown-10. 

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