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Metal free synthesis of functionalized 1-aryl isoquinolines via iodine mediated oxidative dehydrogenation and ring opening of lactam in isoindoloisoquinolinones

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Abstract

A facile and convenient method for the synthesis of substituted 2-(isoquinolin-1-yl)benzoic acids from isoindoloisoquinolinones in the presence of molecular iodine under sealed tube condition at 100\(^{\circ }\hbox {C}\) has been developed. This methodology involves the oxidative dehydrogenation and ring opening of hydroxy lactam/methoxy lactam to furnish the 2-(isoquinolin-1-yl)benzoic acids. Some of these acids are successfully cyclized to furnish the azabenzanthrone derivatives, the potential precursors for the synthesis of menisporphine alkaloids and daurioxoisoaporphines.

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SYNOPSIS Metal-free synthesis of 1-aryl isoquinolines, which are synthetic precursors for azabenzanthrones or menisporphines, from isoindoloisoquinolinones using iodine under sealed tube conditions is reported. This methodology is successfully utilized to synthesize the 1-azabenzanthrone and analogue of menisporphine, i.e., 5-methoxy-6-hydroxy-1-azabenzanthrone.

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Acknowledgements

We thank DST and CSIR, New Delhi, India for financial support. K.M.M.A. thanks UGC, New Delhi for SRF. We gratefully acknowledge the CIF, Pondicherry University for NMR/IR data. DST-FIST program, Department of Chemistry, Pondicherry University is gratefully acknowledged for HRMS. We also acknowledge UGC for the award of SAP (DSA) program to the Department of Chemistry, Pondicherry University. We acknowledge IPLS program, Pondicherry University. Funding was provided by Science and Engineering Research Board (Grant No. SR/S1/OC-04/2011(G); Dated: 25/08/2011), Council of Scientific and Industrial Research (Grant No. 02(0027)/11/EMR-II).

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  1. Department of Chemistry, Pondicherry University, Puducherry, 605 014, India

    Kamsali Murali Mohan Achari, Muthupandi Karthick & Chinnasamy Ramaraj Ramanathan

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  1. Kamsali Murali Mohan Achari
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Correspondence to Chinnasamy Ramaraj Ramanathan.

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Achari, K.M.M., Karthick, M. & Ramanathan, C.R. Metal free synthesis of functionalized 1-aryl isoquinolines via iodine mediated oxidative dehydrogenation and ring opening of lactam in isoindoloisoquinolinones. J Chem Sci 129, 679–690 (2017). https://doi.org/10.1007/s12039-017-1301-7

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