Methylierung von 4‐Hydroxy‐4‐(2‐piperidyl)‐4 H ‐pyrazolo [1,5‐ a ]indol mit Formaldehyd und Ameisensäure. 11. Mitteilung über metallorganische Reaktionen und Folgeprodukte | Zendy

Rihs Grety | Zendy; Fuhrer Hermann | Zendy; Marxer Adrian | Zendy

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Methylierung von 4‐Hydroxy‐4‐(2‐piperidyl)‐4 H ‐pyrazolo [1,5‐ a ]indol mit Formaldehyd und Ameisensäure. 11. Mitteilung über metallorganische Reaktionen und Folgeprodukte

Author(s) -

Rihs Grety,

Fuhrer Hermann,

Marxer Adrian

Publication year - 1981

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19810640316

Subject(s) - chemistry , formic acid , formaldehyde , ketone , ring (chemistry) , indole test , nuclear magnetic resonance spectroscopy , spectroscopy , stereochemistry , medicinal chemistry , organic chemistry , physics , quantum mechanics

In the 10 th communication of this series [1] the synthesis of 4‐hydroxy‐4‐(2‐piperidyl)‐4 H ‐pyrazolo[1,5‐ a ]indole ( 4 ) was described (Scheme) . Surprisingly enough, methylation of this compound with formaldehyde and formic acid led via ring closure and a subsequent rearrangement to a pentacyclic ketone. By means of 13 C‐NMR.‐spectroscopy and mass spectroscopy, this ketone could be identified as a indolizino‐pyrazolo‐indole ( 9 ). Its structure and configuration were determined by X‐ray structure analysis.

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