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. 2020 Sep 28;10(59):35681-35691.
doi: 10.1039/d0ra06537d.

Gold(iii) promoted formation of dihydroquinazolinones: double X-H activation by gold

Veerabhushanam Kadiyala  1   2 , Perla Bharath Kumar  1   2 , Komalla Sunil  1   2 , Chittala Emmaniel Raju  1   2 , Balasubramanian Sridhar  3 , Galla V Karunakar  1   2
Affiliations

Gold(iii) promoted formation of dihydroquinazolinones: double X-H activation by gold

Veerabhushanam Kadiyala et al. RSC Adv. .

Abstract

An efficient 2-furyl gold-carbene promoted synthetic method was developed for the formation of dihydroquinazolinones from enynones by dual insertion of anthranilamides. In this organic transformation a new C-O and two C-N bond formations occurred and dihydroquinazolinones were obtained with a quaternary centre in moderate to very good yields in one-pot synthesis.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. Selected examples of important molecules containing dihydroquinazolinone core skeleton.
Scheme 1
Scheme 1. Synthetic transformations of enynones.
Scheme 2
Scheme 2. Reaction of enynone (1a) with anthranilamides (2a) for formation of 3aa [CCDC 1863534].
Scheme 3
Scheme 3. (a) Reaction of 1a with heteroaryl amine 2f (eqn (1)); (b) reaction of dimethyl-(2-oxo-6-phenylhex-3-en-5-yn-3-yl)phosphonate 1l with 2a (eqn (2)); (c) gram scale synthesis of product 3a (eqn (3)).
Scheme 4
Scheme 4. Control experiments. aCompound 5 CCDC 1898773.
Scheme 5
Scheme 5. A plausible reaction mechanism.
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