Pteridines. Part XCVII . Synthesis and properties of 6‐thioxanthopterin and 7‐thioisoxanthopterin | Zendy

Mohr Detlev | Zendy; Kazimierczuk Zygmunt | Zendy; Pfleiderer Wolfgang | Zendy

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Pteridines. Part XCVII . Synthesis and properties of 6‐thioxanthopterin and 7‐thioisoxanthopterin

Author(s) -

Mohr Detlev,

Kazimierczuk Zygmunt,

Pfleiderer Wolfgang

Publication year - 1992

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.19920750718

Subject(s) - chemistry , pteridine , hydrolysis , derivative (finance) , alkaline hydrolysis , thio , oxide , stereochemistry , organic chemistry , enzyme , financial economics , economics

6‐Thioxanthopterin ( 13 ) was synthesized in four steps starting from 2‐amino‐4‐(penthyloxy)pteridine ( 3 ) via the 8‐oxide 4 , its subsequent interconversion to the 6‐chloro ( 7 ) and 6‐thio derivative ( 12 ) and final hydrolysis of the pentyloxy group. 7‐Thioisoxanthopterin ( 15 ) was derived analogously from 2‐amino‐4‐(pentyloxy)pteridine‐7(8 H )‐thione ( 14 ) by alkaline hydrolysis. The various 6‐ and 7‐thiopteridines were methylated to give the corresponding 6‐ ( 10, 11 ) and 7‐(methylthio) derivatives ( 16, 17 ). The newly synthesized compounds have been characterized by elemental analyses, their UV spectra, and the determination of the acidic and basic p K a values. The spectral relationships are discussed in detail.

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