A series of novel β-carboline-pyridine conjugates linked though amide and thioamide tethers were synthesized under catalyst-free and metal-free conditions using β-carboline alkaloid; Kumujian C as a template. The tert-butyl hydroperoxide (TBHP)-mediated reaction with 2-aminopyridines provided the amide linked β-carboline-pyridine conjugates whereas the Willgerodt-Kindler reaction in presence of elemental sulfur furnished thioamide tethered analogues. The alkyl, aryl, as well as heteroarylamines underwent Willgerodt-Kindler reaction with Kumujian C to afford diverse β-carboline linked thioamides. Both the protocols avoided the use of toxic metal catalysts and expensive additives to provide the products in moderate to excellent yields in a short duration. Interestingly, the amide linked β-carboline-pyridine conjugates displayed excellent photophysical properties with fluorescence quantum yields (ΦF) up to 38% rendering them as promising candidates for applications in biology and optoelectronic materials. © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim