20763-27-3Relevant academic research and scientific papers
Ring-rearrangement during the Mitsunobu alkylation of phthalazinones and indazolols
Knaack, Martin,Fleischhauer, Ilona,Charpentier, Patricia,Emig, Peter,Kutscher, Bernhard,Mueller, Arndt
, p. 1477 - 1482 (2007/10/03)
The Mitsunobu alkylation of substituted phthalazinones and indazolols with cyclic hydroxy- and hydroxymethyl-substituted amines was investigated. In addition to the expected derivatives ring-narrowed and ring-enlarged rearrangement products were isolated and characterized by NMR spectroscopy. The occurence of these products can be explained by the existence of a bicyclic intermediate. The results of the reaction of phthalazinones with optically active amine compounds show a stereospecific reaction mechanism. The reaction of the phthalazinones leads to N-substituted products, while in the case of the indazolols O-substituted derivatives were isolated. A postulated bicyclic intermediate, 1-methyl-1-azoniabicyclo[3.2.0]heptane, was synthesized as chloride. VCH Verlagsgesellschaft mbH, 1996.
HETEROCYCLIC ETHERS DERIVED FROM 6,11-DIHYDRODIBENZOTHIEPIN-11-OLS AND 4,9-DIHYDROTHIENO-2-BENZOTHIEPIN-4-OL; A NEW SERIES OF POTENTIAL ANTIDEPRESSANTS AND ANTIHISTAMINE AGENTS
Polivka, Zdenek,Metys, Jan,Protiva, Miroslav
, p. 2034 - 2049 (2007/10/02)
Reactions of 11-chloro-6,11-dihydrodibenzothiepin and methanesulfonates of 6,11-dihydrodibenzothiepin-11-ol (I), its 2-methyl derivative II and 4,9-dihydrothieno-2-benzothiepin-4-ol (III) with 1-methylpiperidin-4-ol, 1-methylperhydroazepin-4-ol (XIX), and tropine gave the ethers V-X.Their methanesulfonates were pharmacologically tested and showed antireserpine, anticataleptic, and antihistamine activities of various degree.The most active compounds were the ethers V and VI.
