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C(6)N(7)‐cyclized purines
Author(s) -
Griengl H.,
Hayden W.,
Plessing A.
Publication year - 1984
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.5570210212
Subject(s) - chemistry , thionyl chloride , derivative (finance) , chloride , alkyl , medicinal chemistry , purine metabolism , organic chemistry , stereochemistry , financial economics , economics , enzyme
By reaction of 6‐[ N ‐(2‐hydroxyethyl)‐ N ‐methyl]aminopurine ( 2a ) and of the corresponding 3‐hydroxypropyl derivative 2b with thionyl chloride a bridge to N(1) is formed yielding 5 and 6 , respectively, whereas from 6‐[ N ‐(4‐hydroxybutyl)‐ N ‐methyl]aminopurine ( 2c ) the 4‐chlorobutyl compound 4 is obtained, which cyclizes in alkaline medium to the C(6)‐N(7) bridged compound 7 . A related cyclization to 11a–11f is observed when 6‐chloropurines are reacted with 3‐alkyl‐1,3‐oxazolidines or 3‐methyl‐1,3‐thiazolidine.