Synthesis of 7-methyl-6-indolopterin and 7-methyl-6-indoloquinoxaline. Issue 18 (16th September 2016)

• Record Type: Journal Article
• Authors: Goswami, Shyamaprosad; Das, Manas Kumar; Maity, Annada C.; Quah, Ching Kheng; Fun, Hoong-Kun
• Is Part Of: Synthetic communications. Volume 46:Issue 18(2016)
• Page Start: 1529
• Page End: 1536
• Publication Date: 2016-09-16
• Subjects: Indole -- indolopterin -- indoloquinoxaline -- pterin -- quinoxaline; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2016.1215467
• Languages: English
• ISSNs: 0039-7911

Abstract

ABSTRACT: 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. GRAPHICAL ABSTRACT: