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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 50, 2020 - Issue 15
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Articles

Synthesis and spectroscopic studies of methoxy-substituted phenylthienylnicotinamidines

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Pages 2355-2375 | Received 29 Feb 2020, Published online: 18 Jun 2020
 

Abstract

Five thienylnicotinamidine derivatives 5a–e were prepared from their corresponding nicotinonitriles 3a–e on treatment with lithium trimethylsilylamide [LiN(TMS)2] followed by hydrolysis using ethanolic/HCl (gas). The nicotinonitriles 3a–e were prepared via Suzuki coupling reaction of bromothienyl derivative 1 with the appropriate phenylboronic acids 2a–e. The DFT calculation was used to optimize the geometric structure of the newly synthesized nicotinamidines. The comparison of DFT/B3LYP calculated spectral data (1H-NMR and 13C-NMR) with the experimental data showed acceptable agreement. Mass fragmentation patterns of 3,4-dimethoxyphenyl, 3,5-dimethoxyphenyl, and 3,4,5-trimethoxyphenyl thienylnicotinamidine derivatives were investigated.

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Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

The research project [no. MU-SCI-18-13] was funded from research unit, Mansoura University, Mansoura, Egypt.

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