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Relevant academic research and scientific papers

Unusual Fragmentation of 1,1,2,2,3,3-Hexamethylindan. Methyl Group Equilibration and Multi-step Skeletal Rearrangements in the (1+) Ions Prior to the Formation of t-C4H9(1+) Other Fragment Ions

Based on the surprising observation of an intense C4H9(1+) (m/z 57) peak in the electron impact mass spectrum, the fragmentation of 1,1,2,2,3,3-hexamethylindan (2) was studied by mass-analysed ion kinetic energy spectrometry of its deuterium-labelled analogues.While methyl loss from ions (1+). occurs with high selectivity (92percent) from the positions 1 and 3 without any rearrangement, ions (1+) undergo complete equilibration of the five methyl groups as intact entities.Subsequent multi-step skeletal rearrangement of the (1+) ions leads to formation of tert-butyl ions and to the loss of isobutene and propene, again without concomitant hydrogen exchange.Several kinetic isotope effects and also probably a thermodynamic isotope effect associated with each of these fragmentation processes have been found and their origin is discussed.The possibility of the formation of ion-neutral complexes and is considered on the basis of the labelling and reactivity pattern.

FLUORINATED TRICYCLIC NEUROLEPTICS WITH PROLONGED ACTION: DERIVATIVES AND ANALOGUES OF 2-(4-(7-FLUORO-2-ISOPROPYL-10,11-DIHYDRODIBENZOTHIEPIN-11-YL)PIPERAZINE-1-YL)ETHANOL

The preparation of 4-fluoro-2-nitrobenzonitrile (V), an intermediate in the synthesis of the title compound I, from 4-fluoro-2-nitroaniline via 5-fluoro-2-iodonitrobenzene (VII) was elaborated.Syntheses of 1,1,1,3,3,3-hexadeutero-2-propyl (XX) and 1,3,4-trideutero (XXVIII) analogues of compound I from hexadeuteroacetone, and pentadeuterobromobenzene, respectively, were carried out.Compound I was esterified with acetic anhydride, decanoic acid and 3,4,5-trimethoxybenzoyl chloride to give the esters II-IV.Acylation of compound XXX with acetyl chloride, 4-fluorophenoxyacetyl chloride and (4-fluorophenylthio)acetyl chloride and the following reduction of the amides with lithium aluminium hydride gave compounds XXXII, XXXIX, and XL.Substitution reactions of 11-chloro-7-fluoro-2-isopropyl-10,11-dihydrodibenzothiepin with the corresponding N-monosubstituted piperazines resulted in compounds XXXIII-XXXV, XXXVII, XXXVIII, XLI and XLII.Alkylation of XXX with 2-(2-chloroethyl)-1,3-dioxolane afforded compound XXXVI.Pharmacological testing of the new compounds, derivatives and analogues of the neuroleptic agent isofloxythepin (I), for discoordinating and cataleptic activities, showed especially for compounds II, XXXIV and XXXVI very intensive and long-lasting effects.The decanoate III has properties of a depot neuroleptic agent.