Morita-Baylis-Hillman reaction of 3-formyl-9 H-pyrido[3,4- b]indoles and fluorescence studies of the products

Nisha Devi; Virender Singh

doi:10.3762/bjoc.18.92

Morita-Baylis-Hillman reaction of 3-formyl-9 H-pyrido[3,4- b]indoles and fluorescence studies of the products

Beilstein J Org Chem. 2022 Jul 26:18:926-934. doi: 10.3762/bjoc.18.92. eCollection 2022.

Authors

Nisha Devi¹, Virender Singh²

Affiliations

¹ Department of Chemistry, DAV University, Jalandhar-Pathankot National Highway (NH 44), Jalandhar, 144012, Punjab, India.
² Department of Chemistry, Central University of Punjab, Bathinda, India.

Abstract

β-Carboline is a privileged class of the alkaloid family and is associated with a broad spectrum of biological properties. 3-Formyl-9H-pyrido[3,4-b]indole is a such potent precursor belonging to this family which can be tailored for installing diversity at various positions of β-carboline to generate unique molecular hybrids of biological importance. The present work is a step towards this and assimilates the results related to the exploration of 3-formyl-9H-β-carbolines for the synthesis of β-carboline C-3 substituted MBH adducts followed by evaluation of their fluorescent characteristic. The effect of contact time, solvent system, concentration and substituents was also studied during investigation of fluorescence properties of these derivatives.

Keywords: DABCO; MBH reaction; Michael addition; fluorescence; structure–fluorescence activity relationship; β-carboline.

Grants and funding

N. D. acknowledges the financial support from MHRD, New Delhi in the form of Senior Research fellowship. V. S. gratefully acknowledges the financial support in the form of research grant from DST (CS-361/2011), DST-FIST (CSI-228/2011) and CSIR (02(0202)/14/EMR-II), New Delhi (India).