Synthesis, spectroscopic characterization, and computational studies of   2-cyano-6-hydroxybenzothiazole: a key synthetic intermediate of firefly   luciferin

Ghasem SHAHMORADI; Saeid AMANI

Article Details

Synthesis, spectroscopic characterization, and computational studies of 2-cyano-6-hydroxybenzothiazole: a key synthetic intermediate of firefly luciferin

Authors:

Ghasem SHAHMORADI | Saeid AMANI

Publisher:

TUBITAK

Main Topics:

Applied physics

Journal:

Turkish Journal of Chemistry 2018 Vol.42 Issue 6, pp.1499-1517

Document Type:

Article

Publication Date:

11/2018

Document Language:

English

Document ID (Org No.):

2000725945

Frequency:

Bimonthly

eISSN:

1303-6130

pISSN:

1300-0527

Abstract:

 

Firefly luciferin is widely applied as a biotechnological tool for   visualizing various biological processes in vitro and in vivo. Chemically,   2-cyano-6-hydroxybenzothiazole, as a key synthetic intermediate of firefly   luciferin, is obtained from 2-cyano-6-methoxybenzothiazole by changing the   methoxy with a hydroxy group. However, this approach is costly and not   suited for large-scale synthesis. Here we report cost-effective and   efficient syntheses of 2-cyano-6-hydroxybenzothiazole through the catalytic   Sandmeyer-type cyanation reaction. Our approach employs diazonium   tetrafluoroborate salt of 2-amino-6-hydroxybenzothiazole as a cyanation   substrate. The cyanation reaction proceeds efficiently under mild conditions   by using Cu(I)/Cu(II)/N,N,N\textquotesingle,N\textquotesingle-tetramethylethylenediamine as a catalyst. In   addition, computational studies of the 2-cyano-6-hydroxybenzothiazole   structure were performed based on the density functional theory method. The   theoretical parameters of the optimized geometry were derived from the   B3LYP/6-311++++++G(d, p) method. Time-dependent density functional theory   was applied to assign the electronic absorption bands observed   experimentally and the 11^{1}H NMR chemical shifts were computed using the   GIAO method. There was a significant relationship between computational   studies and experimental results.

Article Details

Synthesis, spectroscopic characterization, and computational studies of 2-cyano-6-hydroxybenzothiazole: a key synthetic intermediate of firefly luciferin

Authors: Ghasem SHAHMORADI | Saeid AMANI

Publisher: TUBITAK

Main Topics: Applied physics

Journal: Turkish Journal of Chemistry 2018 Vol.42 Issue 6, pp.1499-1517

Document Type: Article

Publication Date: 11/2018

Document Language: English

Document ID (Org No.): 2000725945

Frequency: Bimonthly

eISSN: 1303-6130

pISSN: 1300-0527

Issues

Authors:

Ghasem SHAHMORADI | Saeid AMANI

Publisher:

TUBITAK

Main Topics:

Applied physics

Journal:

Turkish Journal of Chemistry 2018 Vol.42 Issue 6, pp.1499-1517

Document Type:

Article

Publication Date:

11/2018

Document Language:

English

Document ID (Org No.):

2000725945

Frequency:

Bimonthly

eISSN:

1303-6130

pISSN:

1300-0527