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Synthesis of new guanidine derivatives from 2′,3′,4′,9′‐tetrahydrospiro[piperidine‐4,1′‐[1 H ]pyrido[3,4‐ b ]indole]
Author(s) -
Domány Gy.,
Gizur T.,
BartaSzalai G.,
Schön I.,
Szántay Cs.,
Hegedüs B.
Publication year - 1994
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.5570310664
Subject(s) - chemistry , morpholine , piperidine , pyrrolidine , phenylhydrazine , methylhydrazine , indole test , hydrazine (antidepressant) , derivative (finance) , tetrazole , guanidine , semicarbazide , hydroxylamine , medicinal chemistry , stereochemistry , organic chemistry , chromatography , financial economics , economics
The reaction of the isothiourea derivative 2 with methylaminc or pyrrolidine resulted in guanidines 3a‐3b . Using hydrazine under the same conditions the tetrazole derivative 4 was obtained. On reacting 2 with piperidine, morpholine, methylhydrazine, phenylhydrazine, hydroxylamine or sodium hydroxide, cycliza‐tion took place leading to the novel 4‐cyanimino‐1,2,3,4,6,7,12,12b‐octahydro‐3,12b‐ethanopyrim‐ido[1′,6′:1,2]pyrido[3,4‐ b ]indole ( 5 ). Some structural aspects of 5 and other model compounds were analysed mainly by 13 C nmr spectroscopy.