Synthesis of 7‐aza‐5,8,10‐trideazafolic acid and its 4‐amino‐derivative as potential antifolates | Zendy

Wollein Günther | Zendy; Troschütz Reinhard | Zendy

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Synthesis of 7‐aza‐5,8,10‐trideazafolic acid and its 4‐amino‐derivative as potential antifolates

Author(s) -

Wollein Günther,

Troschütz Reinhard

Publication year - 2002

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.5570390613

Subject(s) - chemistry , saponification , derivative (finance) , yield (engineering) , pyrimidine , guanidine , amide , medicinal chemistry , diamine , condensation , organic chemistry , stereochemistry , materials science , physics , financial economics , economics , metallurgy , thermodynamics

o ‐Aminoamide 8 , an intermediate in our multistep synthesisof the title compounds was prepared from 1,3‐diketone 3 . The following condensation of 8 with chloroformamidine‐HCl ( 9 ) gave pyrido[3,4‐ d ]pyrimidine 10 . Dehydratisation of amide 8 led to o ‐aminonitrile 15 , which was cyclocondensated with guanidine ( 16 ) to yield pyrido[3,4‐ d ]pyrimidine‐2,4‐diamine 17 . Coupling of the acids 11 and 18 with diethyl L‐glutamate ( 12 ) and following saponification provided 7‐aza‐5,8,10‐trideazafolic acid 14 and its 4‐amino‐derivative 20 .

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