Syntheses and acid-stimulus responsiveness of aminobenzopyranoxanthene spiroethers

Ryosuke Hosoda; Shinichiro Kamino; Masashi Ueda; Daisuke Sawada

doi:10.3987/COM-18-S(F)66

Syntheses and acid-stimulus responsiveness of aminobenzopyranoxanthene spiroethers

Ryosuke Hosoda, Shinichiro Kamino, Masashi Ueda, Daisuke Sawada

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

Abstract

Novel aminobenzopyranoxanthene spiroethers (ABPX-SEs) based on the spirocyclization of the hydroxymethyl group were synthesized from ABPX spirolactones (ABPX-SLs). The addition of an acid induces a ring-opening reaction to yield two colored monocationic and dicationic spiro-ring species of ABPX. The acid-stimulus responsiveness of the ABPX-SEs is lower than that of ABPX-SLs in polar organic solvents. In addition, the ABPX-SEs exhibit stepwise structural changes of the three equilibrium species at acidic pH, although rapid conversion from the spirolactone to dicationic species occurs in the case of ABPX-SLs.

Original language	English
Pages (from-to)	820-824
Number of pages	5
Journal	Heterocycles
Volume	99
Issue number	2
DOIs	https://doi.org/10.3987/COM-18-S(F)66
Publication status	Published - 2019

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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title = "Syntheses and acid-stimulus responsiveness of aminobenzopyranoxanthene spiroethers",

abstract = "Novel aminobenzopyranoxanthene spiroethers (ABPX-SEs) based on the spirocyclization of the hydroxymethyl group were synthesized from ABPX spirolactones (ABPX-SLs). The addition of an acid induces a ring-opening reaction to yield two colored monocationic and dicationic spiro-ring species of ABPX. The acid-stimulus responsiveness of the ABPX-SEs is lower than that of ABPX-SLs in polar organic solvents. In addition, the ABPX-SEs exhibit stepwise structural changes of the three equilibrium species at acidic pH, although rapid conversion from the spirolactone to dicationic species occurs in the case of ABPX-SLs.",

author = "Ryosuke Hosoda and Shinichiro Kamino and Masashi Ueda and Daisuke Sawada",

note = "Funding Information: This work was supported by a subsidy to promote science and technology in prefectures where nuclear and other power plants are located, from the Ministry of Education, Culture, Sports, Science and Technology (MEXT). This work was also supported in part by JSPS KAKENHI (S) (No. 17H06173). We Publisher Copyright: {\textcopyright} 2019 The Japan Institute of Heterocyclic Chemistry Received",

year = "2019",

doi = "10.3987/COM-18-S(F)66",

language = "English",

volume = "99",

pages = "820--824",

journal = "Heterocycles",

issn = "0385-5414",

publisher = "Japan Institute of Heterocyclic Chemistry",

number = "2",

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T1 - Syntheses and acid-stimulus responsiveness of aminobenzopyranoxanthene spiroethers

AU - Hosoda, Ryosuke

AU - Kamino, Shinichiro

AU - Ueda, Masashi

AU - Sawada, Daisuke

N1 - Funding Information: This work was supported by a subsidy to promote science and technology in prefectures where nuclear and other power plants are located, from the Ministry of Education, Culture, Sports, Science and Technology (MEXT). This work was also supported in part by JSPS KAKENHI (S) (No. 17H06173). We Publisher Copyright: © 2019 The Japan Institute of Heterocyclic Chemistry Received

PY - 2019

Y1 - 2019

N2 - Novel aminobenzopyranoxanthene spiroethers (ABPX-SEs) based on the spirocyclization of the hydroxymethyl group were synthesized from ABPX spirolactones (ABPX-SLs). The addition of an acid induces a ring-opening reaction to yield two colored monocationic and dicationic spiro-ring species of ABPX. The acid-stimulus responsiveness of the ABPX-SEs is lower than that of ABPX-SLs in polar organic solvents. In addition, the ABPX-SEs exhibit stepwise structural changes of the three equilibrium species at acidic pH, although rapid conversion from the spirolactone to dicationic species occurs in the case of ABPX-SLs.

AB - Novel aminobenzopyranoxanthene spiroethers (ABPX-SEs) based on the spirocyclization of the hydroxymethyl group were synthesized from ABPX spirolactones (ABPX-SLs). The addition of an acid induces a ring-opening reaction to yield two colored monocationic and dicationic spiro-ring species of ABPX. The acid-stimulus responsiveness of the ABPX-SEs is lower than that of ABPX-SLs in polar organic solvents. In addition, the ABPX-SEs exhibit stepwise structural changes of the three equilibrium species at acidic pH, although rapid conversion from the spirolactone to dicationic species occurs in the case of ABPX-SLs.

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DO - 10.3987/COM-18-S(F)66

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SN - 0385-5414

VL - 99

SP - 820

EP - 824

JO - Heterocycles

JF - Heterocycles

IS - 2

ER -

Syntheses and acid-stimulus responsiveness of aminobenzopyranoxanthene spiroethers

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