Convenient Cyanation of Diazonium Tetrafluoroborate Salt Toward Firefly Luciferin Precursors. (26th May 2020)

• Record Type: Journal Article
• Authors: Shahmoradi, Ghasem; Amani, Saeid
• Is Part Of: Polycyclic aromatic compounds. Volume 40:Number 3(2020)
• Page Start: 660
• Page End: 669
• Publication Date: 2020-05-26
• Subjects: 2-cyano-6-hydroxybenzothiazole -- 2-cyano-6-methoxybenzothiazole -- cyanation -- sandmeyer reaction; Polycyclic aromatic compounds -- Periodicals; 547
• DOI: 10.1080/10406638.2018.1472109
• Languages: English
• ISSNs: 1040-6638

Abstract

ABSTRACT: In this paper, the high-yielding synthesis of 2-cyano-6-methoxybenzothiazole and 2-cyano-6-hydroxybenzothiazole through catalytic Sandmeyer cyanation was described. In this Sandmeyer type reaction, 2-amino-6-methoxybenzo-thiazole and 2-amino-6-hydroxybenzothiazole were converted to the corresponding diazonium tetrafluoroborate salt and subsequently cyanated in the presence of Cu(I)/Cu(II)/ N, N, N′, N′-tetramethyl ethylenediamine as a catalyst. This protocol features mild reaction conditions, high yielding, short reaction time and capability for large-scale synthesis. In addition, a direct, more efficient and economical approach for 2-cyano-6-hydroxybenzothiazole was presented.