Synthesis of 7-methyl-6-indolopterin and 7-methyl-6-indoloquinoxaline

The first syntheses of indolopterin and indoloquinoxaline, two important and dissimilar diheterocycles linking C-2 of indole with C-6 of pterin (significant positions for showing biological activity), and quinoxaline, respectively, have been achieved based on two classical reactions. The introductio...

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Bibliographic Details
Published inSynthetic communications Vol. 46; no. 18; pp. 1529 - 1536
Main Authors Goswami, Shyamaprosad, Das, Manas Kumar, Maity, Annada C., Quah, Ching Kheng, Fun, Hoong-Kun
Format Journal Article
LanguageEnglish
Published PHILADELPHIA Taylor & Francis 16.09.2016
Taylor & Francis Ltd
Subjects
Chemistry
Chemistry, Organic
Indole
indolopterin
indoloquinoxaline
Physical Sciences
pterin
quinoxaline
Science & Technology
indoloquinoxaline
indolopterin
quinoxaline
Indole
pterin
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Summary:The first syntheses of indolopterin and indoloquinoxaline, two important and dissimilar diheterocycles linking C-2 of indole with C-6 of pterin (significant positions for showing biological activity), and quinoxaline, respectively, have been achieved based on two classical reactions. The introduction of a keto methyl group on to the 6-position of pterin and quinoxaline followed by Fischer indole synthesis led to these target diheterocycles. These indole-substituted diheterocycles will significantly increase the electron density on the pterin-5-N and quinoxazoline-2-N, which may change the redox properties of pterin and quinoxaline, and also the electron-withdrawing pterin or quinoxazoline should make the indole NH more acidic.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2016.1215467