65999-60-2Relevant articles and documents
Dibenzo[b,f]oxepin-10(11H)-one and dibenzo[b,f]thiepin-10(11H)-one as useful synthons in the synthesis of various dibenzo[e,h]azulenes
Pesic, Dijana,Landek, Ivana Ozimec,Rupcic, Renata,Modric, Marina,Dzapo, Iva,Trojko, Rudolf,Mercep, Mladen,Mesic, Milan
, p. 243 - 252 (2012)
The present review focuses on dibenzo[b,f]oxepin-10(11H)-one (I, X = O) and dibenzo[b,f]thiepin-10(11H)-one (I, X = S) as common synthons in the efficient synthesis of various dibenzoxepino[4,5- and dibenzothiepino[4,5]-fused five-membered heterocycles: [2,3] fused thiophene (II), [3,4] fused thiophene (III), furan (IV), pyrrole (V), imidazole (VI), pyrazole (VII), oxazole (VIII), and thiazole (IX). The potential of I to be converted into reactive intermediates that readily undergo heteroaromatic annulation reactions by cyclocondensation with proper binucleophiles allows formation of a range of enumerated functionalized dibenzo[e,h]azulene [4] structures (II-IX). Dibenzo[e,h]azulenes as heterotetracyclic scaffold can be exploited in further modifications to obtain compounds with altered physicochemical and biological profile. Copyright
Novel tetracyclic imidazole derivatives: Synthesis, dynamic NMR study, and anti-inflammatory evaluation
Rupcic, Renata,Modric, Marina,Hutinec, Antun,Cikos, Ana,Stanic, Barbara,Mesic, Milan,Pesic, Dijana,Mercep, Mladen
experimental part, p. 640 - 656 (2010/08/20)
A series of tetracyclic imidazole derivatives 9a-9v and 10a-10h are prepared by multistep route starting from the known tricyclic diketones 2a-2d. Intermediary dibenzooxepin[4,5-d]imidazoles (3a, 3c) and dibenzothiepin[4,5-d] imidazoles (3b, 3d) are N-protected to 4e, 4f and to the isomeric compounds 5a, 5b and 6a, 6b. The isomeric compounds 5 and 6 are separated. Compounds 4, 5, and 6 are formylated at C(2) to afford 7a-7j. In the last steps, aldehyde group is reduced, then alkylated to the two sets of isomeric ω-dimethylaminoalkyl derivatives 9a-9v. N-deprotection of 9i-9v led to the compounds 10a-10h. Assignment of the syn/anti structure to 5a and 6a was supported by 1D selective ROESY NMR spectra, whereas conformational mobility for the selected representatives 8a and 8b is studied by dynamic NMR. Activation energies (energy barriers for interconversion) are determined to be ～11.5 and 16.2 kcal/mol, respectively. A series of derivatives 9 and 10 were tested in vitro for their anti-inflammatory activity.
8-CHLORO AND 8-METHYLTHIO DERIVATIVES OF 10-PIPERAZINO-10,11-DIHYDRODIBENZOTHIEPINS; NEW COMPOUNDS AND NEW PROCEDURES
Jilek,Jiri,Pomykacek, Josef,Prosek, Zdenek,Holubek, Jiri,Svatek, Emil,et al
, p. 906 - 927 (2007/10/02)
The resolution of racemic clorothepin (Ia) was repeated and the water-soluble methanesulfonates of (S)(+)-clorothepin and (R)(-)-clorothepin were prepared which were used in recent studies of the stereoselectivity of action of this neuroleptic agent.Alkylation of the secondary amine VIa with 2-chloroethyl decanoate resulted in noroxyclothepin decanoate IVa whose basically catalyzed ethanolysis afforded smoothly the amino alcohol IIa.Reactions of amines VIa and VIb with 1,2-butene oxide gave the amino alcohols VIIab.Alkylation of the amine VIa with 5-bromopentan-2-oneand the following reduction of the amino ketone IXa formed gave the amino alcohol VIIIa.Amino alcohols IIa and IIIb were transformed by treatment with thionyl chloride to the chloroalkylamines Xa and XIb which were used for the synthesis of mandelates XIIa, XIIIb and benzilates XIVa, XVb derived from noroxyclothepin IIa and oxyprothepin IIIb.A substitution reaction of 2,11-dichloro-10,11-dihydrodibenzothiepin with 1,4-diazabicyclononane led to the clorothepin analogue XVI.From 2-chlorodibenzothiepin-10(11 H)-one XVII via the 11-bromo derivative XVIII the amino ketone XIX was prepared.While its reduction with sodium borohydride gave the cis-amino alcohol XXI, the reduction with diborane gave the trans-amino alcohol XXII.The pharmacological properties of the new piperazine derivatives are described; some of them showed a high degree of neuroleptic activity of various profile.
