Laccase-Catalyzed Domino Reaction between Catechols and 6-Substituted 1,2,3,4-Tetrahydro-4-oxo-2-thioxo-5-pyrimidinecarbonitriles for the Synthesis of Pyrimidobenzothiazole Derivatives

Publication Type

Journal contribution (peer reviewed)

Authors

Abdel-Mohsen, H. T.; Conrad, J.; Beifuss, U.

Year of publication

2013

Published in

J. Org. Chem.

Band/Volume

78/

DOI

10.1021/jo401193e

Page (from - to)

7986-8003

The laccase-catalyzed domino reaction between catechols and 6-substituted 1,2,3,4-tetrahydro-4-oxo-2-thioxo-5-pyrimidinecarbonitriles using aerial O₂ as the oxidant delivers new pyrimidobenzothiazole derivatives. The complete structure elucidation of the ring-proton deficient heterocyclic products and the unambiguous determination of the regioselectivity of the reactions have been achieved by extended NMR spectroscopic methods including HSQMBC, super long-range HMBC, and ¹⁵N measurements.