Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2020, Issue 8, Pages 1023-1041Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201901908
Keywords
B-Carboline; Benzothiazole; Iodine; Fluorescent; Thiazolocarbazole; Photophysical properties
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Funding
- Council of Scientific & Industrial Research (CSIR), New Delhi, India
- Council of Scientific & Industrial Research New Delhi, India [(02)0356/19/EMR-II, (02)0202/14/EMR-II]
- Department of Science and Technology, Science and Engineering Research Board, New Delhi [EMR/2017/000155, SB/FT/CS-188/2011, DST-FIST CSI-228/2011]
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A Simple, convenient and highly efficient I-2-catalysed approach has been unfolded towards the synthesis of highly fluorescent beta-carboline C-1(3)-tethered thiazolo[4,5-c]carbazoles, naphtho[2,1-d]thiazoles and benzothiazole derivatives using Kumujian C as a template. This domino strategy proceeds through assembly of 1-formyl-9H-beta-carbolines, arylamines and elemental sulfur via formation of one C-N and two C-S bonds in a single operation. Importantly, the methodology was found applicable to beta-carboline acetals also. A diversely substituted library of 37 beta-carboline tethered arylthiazole hybrids was prepared in excellent yields. The strategy was found appropriate for gram scale synthesis also. The photophysical properties of these fluorophores were also estimated and showed excellent fluorescence properties with quantum yield (phi(F)) up to 92 %.
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