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Harari M, Couly F, Fruit C, et al. Pd-Catalyzed and Copper Assisted Regioselective Sequential C2 and C7 Arylation of Thiazolo[5,4-f]quinazolin-9(8H)-one with Aryl Halides. Org Lett. 2016;18(13):3282-5doi: 10.1021/acs.orglett.6b01552.
Harari, M., Couly, F., Fruit, C., & Besson, T. (2016). Pd-Catalyzed and Copper Assisted Regioselective Sequential C2 and C7 Arylation of Thiazolo[5,4-f]quinazolin-9(8H)-one with Aryl Halides. Organic letters, 18(13), 3282-5. https://doi.org/10.1021/acs.orglett.6b01552
Harari, Marine, et al. "Pd-Catalyzed and Copper Assisted Regioselective Sequential C2 and C7 Arylation of Thiazolo[5,4-f]quinazolin-9(8H)-one with Aryl Halides." Organic letters vol. 18,13 (2016): 3282-5. doi: https://doi.org/10.1021/acs.orglett.6b01552
Harari M, Couly F, Fruit C, Besson T. Pd-Catalyzed and Copper Assisted Regioselective Sequential C2 and C7 Arylation of Thiazolo[5,4-f]quinazolin-9(8H)-one with Aryl Halides. Org Lett. 2016 Jul 01;18(13):3282-5. doi: 10.1021/acs.orglett.6b01552. Epub 2016 Jun 17. PMID: 27314437.
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Org Lett. 2016 Jul 01;18(13):3282-5. doi: 10.1021/acs.orglett.6b01552. Epub 2016 Jun 17.

Pd-Catalyzed and Copper Assisted Regioselective Sequential C2 and C7 Arylation of Thiazolo[5,4-f]quinazolin-9(8H)-one with Aryl Halides.

Organic letters

Marine Harari, Florence Couly, Corinne Fruit, Thierry Besson

Affiliations

  1. Normandie Univ, UNIROUEN, INSA Rouen, CNRS, COBRA, 76000 Rouen, France.

PMID: 27314437 DOI: 10.1021/acs.orglett.6b01552

Abstract

A selective functionalization of thiazolo[5,4-f]quinazolin-9(8H)-one has been developed through sequential activation of C-H bonds to furnish diarylated compounds. This strategy allows the regioselective C2 and C7 arylation by a judicious choice of coupling partners and bases, requiring no additional ligands or directing groups. Differently substituted N(8)-benzylated-2,7-diaryl-thiazoloquinazolin-9(8H)-ones were thereby obtained in a facile manner. A one-pot procedure was also performed. These protocols provide a synthetically useful route for late-stage functionalization of this highly valuable scaffold, required in drug discovery.

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