(Chemical Equation Presented) Different anilides derived from carboxylic acids and substituted anilines have been submitted to the photochemically induced Fries rearrangement giving the corresponding o-amino phenones under conditions that are compatible with the presence of acid-labile groups (such as N-Boc or TBDMSO) on R1 and R3. These compounds, not easily obtained in other ways, are useful building blocks for the preparation of benzocondensated heterocycles. After coupling with N-Boc amino acids and TFA-mediated deprotection, the products cyclized to the corresponding 3,5-disubstituted 1,4-benzodiazepin-2-ones, privileged structures predominantly active in the central nervous system. The same results were obtained by coupling with N-Cbz-protected α-amino acids followed by microwave assisted hydrogenolysis. When the Fries rearrangement was carried out on the anilide derived from N-Boc-Ala-OH and the further coupling done with N-Cbz-(OMe)Asp-OH, the formed benzodiazepines could be inserted in a peptide chain for the preparation of conformationally constrained peptidomimetics. © 2006 American Chemical Society.

Ferrini, S., Ponticelli, F., Taddei, M. (2006). Rapid approach to 3,5-disubstituted 1,4-benzodiazepine via the photo-Fries rearrangment of anilides. JOURNAL OF ORGANIC CHEMISTRY, 71(24), 9217-9220 [10.1021/jo0614442].

Rapid approach to 3,5-disubstituted 1,4-benzodiazepine via the photo-Fries rearrangment of anilides

Ponticelli, Fabio;Taddei, Maurizio
2006-01-01

Abstract

(Chemical Equation Presented) Different anilides derived from carboxylic acids and substituted anilines have been submitted to the photochemically induced Fries rearrangement giving the corresponding o-amino phenones under conditions that are compatible with the presence of acid-labile groups (such as N-Boc or TBDMSO) on R1 and R3. These compounds, not easily obtained in other ways, are useful building blocks for the preparation of benzocondensated heterocycles. After coupling with N-Boc amino acids and TFA-mediated deprotection, the products cyclized to the corresponding 3,5-disubstituted 1,4-benzodiazepin-2-ones, privileged structures predominantly active in the central nervous system. The same results were obtained by coupling with N-Cbz-protected α-amino acids followed by microwave assisted hydrogenolysis. When the Fries rearrangement was carried out on the anilide derived from N-Boc-Ala-OH and the further coupling done with N-Cbz-(OMe)Asp-OH, the formed benzodiazepines could be inserted in a peptide chain for the preparation of conformationally constrained peptidomimetics. © 2006 American Chemical Society.
2006
Ferrini, S., Ponticelli, F., Taddei, M. (2006). Rapid approach to 3,5-disubstituted 1,4-benzodiazepine via the photo-Fries rearrangment of anilides. JOURNAL OF ORGANIC CHEMISTRY, 71(24), 9217-9220 [10.1021/jo0614442].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11365/19489
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