Regioselective synthesis of new 5H,10H-dipyrimido[2,1-b:4′,5′-d][1,3]thiazine: a combined experimental and computational study

ABSTRACT

Several derivatives of the novel tricyclic system ‘dipyrimido[2,1-b:4′,5′-d][1,3]thiazine’ were synthesized via inter- and intramolecular heterocyclization of 2,4-dichloro-5-(chloromethyl)-6-methylpyrimidine and 6-amino-4-aryl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile in short reaction times under mild conditions. An x-ray analysis together with computational calculations was performed to gain an in-depth understanding of regioselectivity of the reaction.

GRAPHICAL ABSTRACT

KEYWORDS:

• Dipyrimido[2,1-b:4′,5′-d] [1,3]thiazine
• heterocyclization
• regioselectivity
• computational calculations

Acknowledgements

The authors are gratefully acknowledged Ferdowsi University of Mashhad for financial support of this project (3/41282).

Disclosure statement

No potential conflict of interest was reported by the authors.

ORCID

Mehdi Bakavoli http://orcid.org/0000-0003-2801-1118

Hossein Eshghi http://orcid.org/0000-0002-8417-220X

Additional information

Funding

This work was supported by Ferdowsi University of Mashhad [grant number 3/41282].