Synthesis and Optical Properties of N-Arylnaphtho- and Anthra[2,3-d]oxazol-2-amines DOI Creative Commons
Yuki Murata,

Masato Kawakubo,

Atsuko Maruyama

и другие.

Molecules, Год журнала: 2025, Номер 30(2), С. 319 - 319

Опубликована: Янв. 15, 2025

Oxazole, a versatile and significant heteroarene, serves as bridge between synthetic organic chemistry applications in the medicinal, pharmaceutical, industrial fields. Polycyclic aromatic compounds with amino groups substituted at 2-position of an oxazole, such 2-aminonaphthoxazoles, are expected to be functional probes, but their methods extremely limited. Herein, we describe electrochemical reactions 3-amino-2-naphthol or 3-amino-2-anthracenol isothiocyanates DMSO, using graphite electrode anode platinum cathode presence potassium iodide (KI), which afford N-arylnaphtho- N-arylanthra[2,3-d]oxazol-2-amines via cyclodesulfurization. This reaction is first example synthesis 2-aminoxazole-based polycyclic reaction. An examination spectroscopic properties oxazoles revealed that λabs value tetracyclic was redshifted relative tricyclic oxazoles. Moreover, synthesized naphthalene/anthracene-fused exhibited extended π-conjugated skeletons fluoresced 340–430 nm region chloroform.

Язык: Английский

Synthesis and Optical Properties of N-Arylnaphtho- and Anthra[2,3-d]oxazol-2-amines DOI Creative Commons
Yuki Murata,

Masato Kawakubo,

Atsuko Maruyama

и другие.

Molecules, Год журнала: 2025, Номер 30(2), С. 319 - 319

Опубликована: Янв. 15, 2025

Oxazole, a versatile and significant heteroarene, serves as bridge between synthetic organic chemistry applications in the medicinal, pharmaceutical, industrial fields. Polycyclic aromatic compounds with amino groups substituted at 2-position of an oxazole, such 2-aminonaphthoxazoles, are expected to be functional probes, but their methods extremely limited. Herein, we describe electrochemical reactions 3-amino-2-naphthol or 3-amino-2-anthracenol isothiocyanates DMSO, using graphite electrode anode platinum cathode presence potassium iodide (KI), which afford N-arylnaphtho- N-arylanthra[2,3-d]oxazol-2-amines via cyclodesulfurization. This reaction is first example synthesis 2-aminoxazole-based polycyclic reaction. An examination spectroscopic properties oxazoles revealed that λabs value tetracyclic was redshifted relative tricyclic oxazoles. Moreover, synthesized naphthalene/anthracene-fused exhibited extended π-conjugated skeletons fluoresced 340–430 nm region chloroform.

Язык: Английский

Процитировано

0