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Synthesis of pyrazole analogues of isoaptazepine
Author(s) -
Massa Silvio,
Artico Marino,
Mai Antonello,
Mancuso Antonella,
Corelli Federico
Publication year - 1992
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570290729
Subject(s) - chemistry , pyrazole , annulation , lithium (medication) , aluminum hydride , derivative (finance) , sulfuric acid , hydride , lithium aluminium hydride , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , metal , medicine , methoxide , financial economics , economics , endocrinology
The synthesis of the novel tetracyclic rings 5 and 6 is described starting from 4‐cyano‐1‐methyl‐5(1 H ‐pyrrol‐1‐yl)‐1 H ‐pyrazole and its 3‐(1 H ‐pyrrol‐1‐yl)‐ isomer, respectively. The pathway employed is based on a one‐pot double annelation reaction involving the transformation of 13 into the required tetracyclic derivative 16 . Lithium aluminum hydride/sulfuric acid reduction of the last compound furnished 5 . A similar way was used for the synthesis of 6 by cyclization of 20 .
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