Synthesis and Optical Properties of <i>N</i>-Arylnaphtho- and Anthra[2,3-<i>d</i>]oxazol-2-amines
Oxazole, a versatile and significant heteroarene, serves as a bridge between synthetic organic chemistry and applications in the medicinal, pharmaceutical, and industrial fields. Polycyclic aromatic compounds with amino groups substituted at the 2-position of an oxazole, such as 2-aminonaphthoxazole...
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2025-01-01
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| author | Yuki Murata Masato Kawakubo Ayumi Maruyama Mio Matsumura Shuji Yasuike |
| author_facet | Yuki Murata Masato Kawakubo Ayumi Maruyama Mio Matsumura Shuji Yasuike |
| author_sort | Yuki Murata |
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| description | Oxazole, a versatile and significant heteroarene, serves as a bridge between synthetic organic chemistry and applications in the medicinal, pharmaceutical, and industrial fields. Polycyclic aromatic compounds with amino groups substituted at the 2-position of an oxazole, such as 2-aminonaphthoxazoles, are expected to be functional probes, but their synthetic methods are extremely limited. Herein, we describe electrochemical reactions of 3-amino-2-naphthol or 3-amino-2-anthracenol and isothiocyanates in DMSO, using a graphite electrode as an anode and a platinum electrode as a cathode in the presence of potassium iodide (KI), which afford <i>N</i>-arylnaphtho- and <i>N</i>-arylanthra[2,3-<i>d</i>]oxazol-2-amines via cyclodesulfurization. This reaction is the first example of synthesis of 2-aminoxazole-based polycyclic compounds using an electrochemical reaction. An examination of the spectroscopic properties of polycyclic oxazoles revealed that the λ<sub>abs</sub> value of the tetracyclic oxazoles was redshifted relative to that of the tricyclic oxazoles. Moreover, synthesized naphthalene/anthracene-fused tricyclic and tetracyclic oxazoles exhibited extended π-conjugated skeletons and fluoresced in the 340–430 nm region in chloroform. |
| format | Article |
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| institution | Kabale University |
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| language | English |
| publishDate | 2025-01-01 |
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| spelling | doaj-art-0b03c84dbdab4ef3815666079fefcbe82025-01-24T13:43:35ZengMDPI AGMolecules1420-30492025-01-0130231910.3390/molecules30020319Synthesis and Optical Properties of <i>N</i>-Arylnaphtho- and Anthra[2,3-<i>d</i>]oxazol-2-aminesYuki Murata0Masato Kawakubo1Ayumi Maruyama2Mio Matsumura3Shuji Yasuike4School of Pharmaceutical Sciences, Aichi Gakuin University, 1-100 Kusumoto-cho, Chikusa-ku, Nagoya 464-8650, JapanSchool of Pharmaceutical Sciences, Aichi Gakuin University, 1-100 Kusumoto-cho, Chikusa-ku, Nagoya 464-8650, JapanSchool of Pharmaceutical Sciences, Aichi Gakuin University, 1-100 Kusumoto-cho, Chikusa-ku, Nagoya 464-8650, JapanSchool of Pharmaceutical Sciences, Aichi Gakuin University, 1-100 Kusumoto-cho, Chikusa-ku, Nagoya 464-8650, JapanSchool of Pharmaceutical Sciences, Aichi Gakuin University, 1-100 Kusumoto-cho, Chikusa-ku, Nagoya 464-8650, JapanOxazole, a versatile and significant heteroarene, serves as a bridge between synthetic organic chemistry and applications in the medicinal, pharmaceutical, and industrial fields. Polycyclic aromatic compounds with amino groups substituted at the 2-position of an oxazole, such as 2-aminonaphthoxazoles, are expected to be functional probes, but their synthetic methods are extremely limited. Herein, we describe electrochemical reactions of 3-amino-2-naphthol or 3-amino-2-anthracenol and isothiocyanates in DMSO, using a graphite electrode as an anode and a platinum electrode as a cathode in the presence of potassium iodide (KI), which afford <i>N</i>-arylnaphtho- and <i>N</i>-arylanthra[2,3-<i>d</i>]oxazol-2-amines via cyclodesulfurization. This reaction is the first example of synthesis of 2-aminoxazole-based polycyclic compounds using an electrochemical reaction. An examination of the spectroscopic properties of polycyclic oxazoles revealed that the λ<sub>abs</sub> value of the tetracyclic oxazoles was redshifted relative to that of the tricyclic oxazoles. Moreover, synthesized naphthalene/anthracene-fused tricyclic and tetracyclic oxazoles exhibited extended π-conjugated skeletons and fluoresced in the 340–430 nm region in chloroform.https://www.mdpi.com/1420-3049/30/2/319electrochemical reactionpolycyclic benzene-fused oxazolecyclodesulfurizationthioureaoptical property |
| spellingShingle | Yuki Murata Masato Kawakubo Ayumi Maruyama Mio Matsumura Shuji Yasuike Synthesis and Optical Properties of <i>N</i>-Arylnaphtho- and Anthra[2,3-<i>d</i>]oxazol-2-amines Molecules electrochemical reaction polycyclic benzene-fused oxazole cyclodesulfurization thiourea optical property |
| title | Synthesis and Optical Properties of <i>N</i>-Arylnaphtho- and Anthra[2,3-<i>d</i>]oxazol-2-amines |
| title_full | Synthesis and Optical Properties of <i>N</i>-Arylnaphtho- and Anthra[2,3-<i>d</i>]oxazol-2-amines |
| title_fullStr | Synthesis and Optical Properties of <i>N</i>-Arylnaphtho- and Anthra[2,3-<i>d</i>]oxazol-2-amines |
| title_full_unstemmed | Synthesis and Optical Properties of <i>N</i>-Arylnaphtho- and Anthra[2,3-<i>d</i>]oxazol-2-amines |
| title_short | Synthesis and Optical Properties of <i>N</i>-Arylnaphtho- and Anthra[2,3-<i>d</i>]oxazol-2-amines |
| title_sort | synthesis and optical properties of i n i arylnaphtho and anthra 2 3 i d i oxazol 2 amines |
| topic | electrochemical reaction polycyclic benzene-fused oxazole cyclodesulfurization thiourea optical property |
| url | https://www.mdpi.com/1420-3049/30/2/319 |
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