917899-26-4Relevant academic research and scientific papers
Synthesis of 3,3-Diarylazetidines by Calcium(II)-Catalyzed Friedel-Crafts Reaction of Azetidinols with Unexpected Cbz Enhanced Reactivity
Denis, Camille,Dubois, Maryne A.J.,Voisin-Chiret, Anne Sophie,Bureau, Ronan,Choi, Chulho,Mousseau, James J.,Bull, James A.
, p. 300 - 304 (2019/01/10)
Azetidines are valuable motifs that readily access under explored chemical space for drug discovery. 3,3-Diarylazetidines are prepared in high yield from N-Cbz azetidinols in a calcium(II)-catalyzed Friedel-Crafts alkylation of (hetero)aromatics and phenols, including complex phenols such as β-estradiol. Electron poor phenols undergo O-alkylation. The product azetidines can be derivatized to drug-like compounds through the azetidine nitrogen and the aromatic groups. The N-Cbz group is crucial to reactivity by providing stabilization of an intermediate carbocation on the four-membered ring.
ARYL-ALKYLAMINES AND HETEROARYL-ALKYLAMINES AS PROTEIN KINASE INHIBITORS
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Page/Page column 195, (2010/11/25)
The invention provides a compound of the formula (II): or a salt, solvate, tautomer or N-oxide thereof; wherein n is 0 or 1; one of Y1 and Y2 is CH and the other is selected from CH, CR8 and N; q is 0, 1 or 2 provided that q is 0 or 1 when Y1 or Y2 is CR8; R1 is an aryl or heteroaryl group of 5 to 10 ring members; R2a and R3a each are hydrogen, C1-4 hydrocarbyl or C1-4 acyl wherein the hydrocarbyl and acyl moieties are optionally substituted by fluorine, hydroxy, amino, methylamino, dimethylamino or methoxy; or NR2aR3a forms an imidazole group or a saturated monocyclic 4-7 membered heterocyclic group optionally containing a second heteroatom ring member selected from O and N; R18 is hydrogen or methyl; R19 is hydrogen or methyl; R24 is hydrogen or R24, R2a and the intervening nitrogen atom and carbon atoms together form an azetidine, pyrrolidine or piperidine ring; R25 is hydrogen or a C1-4 alkyl group wherein the C1-4 alkyl group is optionally substituted by hydroxy or amino provided that there are at least two carbon atoms between the hydroxy or amino group and the oxygen atom to which R25 is attached; and R4 and R5 each are hydrogen or a substituent as defined in the claims
