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. 2019 Sep 25;9(52):30277-30291.
doi: 10.1039/c9ra06212b. eCollection 2019 Sep 23.

Oxone promoted dehydrogenative Povarov cyclization of N-aryl glycine derivatives: an approach towards quinoline fused lactones and lactams

Devidas A More  1   2 , Ganesh H Shinde  1 , Aslam C Shaikh  1 , M Muthukrishnan  1   2
Affiliations

Oxone promoted dehydrogenative Povarov cyclization of N-aryl glycine derivatives: an approach towards quinoline fused lactones and lactams

Devidas A More et al. RSC Adv. .

Abstract

Oxone promoted intramolecular dehydrogenative imino Diels-Alder reaction (Povarov cyclization) of alkyne tethered N-aryl glycine esters and amides has been explored, thus affording biologically significant quinoline fused lactones and lactams. The reaction is simple, scalable, and high yielding (up to 88%). The method was further extended to prepare biologically important luotonin-A analogues and the quinoline core of uncialamycin.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. Examples of pharmaceuticals and natural products containing quinoline-fused lactone/lactam moiety.
Scheme 1
Scheme 1. Intramolecular Povarov cyclization for the synthesis of quinoline fused lactones and lactams.
Scheme 2
Scheme 2. Synthesis of alkyne tethered N-aryl glycine derivatives.
Scheme 3
Scheme 3. Intramolecular Povarov cyclization of N-aryl glycine estersa,b. aReaction conditions: 0.18 mmol 1a, 0.20 mmol oxidant, 5 mol% of Cu(OTf)2, CH3CN (3.0 mL), rt, 12 h; bisolated yields.
Scheme 4
Scheme 4. Intramolecular Povarov cyclisation of N-aryl glycine amides.a,b. aReaction conditions: 0.14 mmol 3a, 0.15 mmol Oxidant, 5 mol% of Cu(OTf)2, CH3CN (3.0 mL), 60 °C, 12 h; bisolated yields; creaction carried out at room temperature for 12 h.
Scheme 5
Scheme 5. A plausible mechanism and control experiment.
Scheme 6
Scheme 6. Utility of the reaction.
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