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. 2019 Feb 4;9(7):3755-3763.
doi: 10.1039/c8ra07517d. eCollection 2019 Jan 25.

An efficient, mild and metal free l-proline catalyzed construction of fused pyrimidines under microwave conditions in water

Manvendra S Kaurav  1 , Pramod K Sahu  1   2 , Praveen K Sahu  2 , Mouslim Messali  3 , Saud M Almutairi  4 , Puran L Sahu  5   6 , Dau D Agarwal  1   2
Affiliations

An efficient, mild and metal free l-proline catalyzed construction of fused pyrimidines under microwave conditions in water

Manvendra S Kaurav et al. RSC Adv. .

Abstract

One-pot condensation of 4-hydroxy coumarins, aldehydes and urea/thiourea to build C-C and C-N bonds is described. Fused pyrimidines have been synthesized under mild reaction conditions using l-proline. The protocol has been performed rapidly and efficiently in water under metal free conditions. Heterocyclic derivatives have been synthesized using the present methodology and avoid the use of hazardous solvents over conventional organic solvents. A proposed mechanism could be established for three component reactions. The present study reveals the first case in which l-proline has been explored as a homogeneous catalyst in the synthesis of fused pyrimidines in water under microwave irradiation. This synthesis involves simple workup and acceptable efficiency. The most notable feature of this protocol is the ability of the catalyst to influence asymmetric induction in the reaction.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. Some drugs with coumarin and pyrimidine core.
Scheme 1
Scheme 1. Synthesis of fused pyrimidines.
Fig. 2
Fig. 2. Comparison of reaction time with respect to yield.
Scheme 2
Scheme 2. Plausible reaction mechanism.
See this image and copyright information in PMC

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