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Simple and efficient synthesis of 4-arylamino-1,3-dioxanes in aqueous medium: a new route for the Prins reaction

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Abstract

Substituted 4-arylamino-1,3-dioxanes were synthesized using a new synthetic protocol of the Prins reaction between aryl amines and acetaldehyde. This one-pot synthesis occurs under catalyst-free conditions in an aqueous medium. By employing condensation of excess acetaldehyde with an aromatic amine in water at 0–5 °C, the corresponding N-aryl-2,6-dimethyl-1,3-dioxan-4-amines are obtained in good yields. Consequently, this is an environmentally benign, simple, efficient, “green” procedure for the preparation of 1,3-dioxanes.

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Scheme 1
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Scheme 2
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Acknowledgments

The authors are thankful to the management of Sree Vidyanikethan Engineering College for their generous support and facilities and also to the management of VIT University, Vellore, for their support. We thank SIF-Chemistry, VIT University, for providing NMR facilities.

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Correspondence to V. Vijayakumar.

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Rambabu, G., Palakshi Reddy, B., Kiran, Y.B. et al. Simple and efficient synthesis of 4-arylamino-1,3-dioxanes in aqueous medium: a new route for the Prins reaction. Res Chem Intermed 41, 8441–8450 (2015). https://doi.org/10.1007/s11164-014-1902-4

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