Calcium-Promoted [3+3] Annulation of Morita-Baylis-Hillman Ketones with 2-Aminobenzothiazoles to Construct Pyrimidobenzothiazoles

17 October 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The reaction of Morita-Baylis-Hillman (MBH) ketones with 2-aminobenzothiazoles is used to construct new analogues of 4H-benzo [4,5] thiazolo [3,2-a] pyrimidine. MBH ketone provides a desirable reactivity with significant outcomes. The mechanism of the reaction involves aza-Michael addition followed by intramolecular cyclization with the removal of a water molecule. This approach tolerates a wide range of substrate scope adequacy, using minimal loading of inexpensive and more abundant Ca(II) catalyst.

Keywords

Pyrimidobenzothiazole
[3+3] Annulation
MBH ketone
2-Aminobenzothiazole

Supplementary materials

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Title
Calcium-Promoted [3+3] Annulation of Morita-Baylis-Hillman Ketones with 2-Aminobenzothiazoles to Construct Pyrimidobenzothiazoles
Description
The reaction of Morita-Baylis-Hillman (MBH) ketones with 2-aminobenzothiazoles is used to construct new analogues of 4H-benzo [4,5] thiazolo [3,2-a] pyrimidine. MBH ketone provides a desirable reactivity with significant outcomes. The mechanism of the reaction involves aza-Michael addition followed by intramolecular cyclization with the removal of a water molecule. This approach tolerates a wide range of substrate scope adequacy, using minimal loading of inexpensive and more abundant Ca(II) catalyst.
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