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

✍ Scribed by Detlev Mohr; Zygmunt Kazimierczuk; Wolfgang Pfleiderer

Book ID
102258150
Publisher
John Wiley and Sons
Year
1992
Tongue
German
Weight
474 KB
Volume
75
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

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.

📜 SIMILAR VOLUMES

Pteridines. Part XLI. Synthesis and prop
Pteridines. Part XLI. Synthesis and properties of 6,7,8-trimethyl-4-thiolumazine
✍ Walter Hübsch; Wolfgang Pfleiderer 📂 Article 📅 1989 🏛 John Wiley and Sons 🌐 German ⚖ 344 KB

The first representative of the &substituted 4-thiolumazine series has been synthesized. In a sequence of reactions, 4,6-dichloropyrimidin-2-( 1 H)-one (1) is first converted into 4-chloro-6-(methylamino)pyrimidin-2( 1H)one (6), then the Cl-atom displaced by the thioxo group ( +7) followed by a coup