Title:
PYRANOQUINAZOLINE DERIVATIVE AND NAPHTHOPYRAN DERIVATIVE
Document Type and Number:
WIPO Patent Application WO/2018/168232
Kind Code:
A1
Abstract:
[Problem] A problem was presented in that conventional photochromic compounds cannot be considered adequate in terms of the coloring/decoloring rate and durability, and the production process therefor has many steps. The present invention provides an industrially applicable photochromic compound that has both a rapid coloring/decoloring reaction and high durability and can also be synthesized at a low cost. [Solution] This compound is characterized in that etheric oxygen atoms are bonded to the carbon atoms at position 1 of a pyranoquinazoline (8H-pyrano[3,2-f]quinazoline) skeleton and position 10 of a naphthopyran (3H-naphtho[2,1-b]pyran) skeleton, said compound having photochromic properties and being a photochromic compound that has both a rapid coloring/decoloring reaction and high durability. Also provided is an industrially applicable photochromic compound that can be synthesized at a low cost.
Inventors:
ABE JIRO (JP)
INAGAKI YUKI (JP)
SUGA TAKAYOSHI (JP)
NAGASAWA HIROTO (JP)
INAGAKI YUKI (JP)
SUGA TAKAYOSHI (JP)
NAGASAWA HIROTO (JP)
Application Number:
PCT/JP2018/003141
Publication Date:
September 20, 2018
Filing Date:
January 31, 2018
Export Citation:
Assignee:
KANTO KAGAKU (JP)
International Classes:
C07D491/052; C07D311/92; C07D519/00; C08F220/18; C09K9/02; G02B1/04; G02B5/23
Domestic Patent References:
| WO2009136668A1 | 2009-11-12 |
Foreign References:
| JPH08176139A | 1996-07-09 | |||
| JP2015127371A | 2015-07-09 | |||
| JP2000229973A | 2000-08-22 | |||
| JPH06135967A | 1994-05-17 | |||
| JPH08295690A | 1996-11-12 | |||
| JP2004210657A | 2004-07-29 | |||
| JP2007525462A | 2007-09-06 | |||
| JP2012501326A | 2012-01-19 | |||
| JP2015137259A | 2015-07-30 |
Other References:
CRANO, J. C. ET AL.: "Photochromic compounds: chemistry and application in ophthalmic lenses", PURE & APPLIED CHEMISTRY, vol. 68, no. 7, January 1996 (1996-01-01), pages 1395 - 1398, XP055544375, ISSN: 0033-4545
ARAI, K. ET AL.: "Rational molecular designs for drastic acceleration of the color-fading speed of photochromic naphthopyrans", CHEMICAL COMMUNICATIONS, vol. 51, no. 15, 2015, pages 3057 - 3060, XP055544377, ISSN: 1359-7345
CHAMONTIN, K. ET AL.: "Synthesis and reactivity of formyl-substituted photochromic 3,3-Diphenyl-[3H]- naphtho[2,1-b]pyrans", TETRAHEDRON, vol. 55, no. 18, 30 April 1999 (1999-04-30), pages 5821 - 5830, XP004163608, ISSN: 0040-4020
OLIVEIRA, M. M. ET AL.: "Remarkable thermally stable open forms of photochromic new N- substituted benzopyranocarbazoles", JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A: CHEMISTRY, vol. 198, no. 2-3, 15 August 2008 (2008-08-15), pages 242 - 249, XP022710250, ISSN: 1010-6030
INAGAKI, Y. ET AL.: "A simple and versatile strategy for rapid color fading and intense coloration of photochromic naphthopyran families", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 139, no. 38, 13 September 2017 (2017-09-13), pages 13429 - 13441, XP055544381, ISSN: 0002-7863
Y.M. SHINOHARAT. ARAI, BULL. CHEM. SOC. JPN., vol. 81, no. 11, 2008, pages 1500 - 1504
Y.M. NORIKANEN., NAKAYAMAN., TAMAOKIT., ARAIU . NAGASHIMA, J. PHYS. CHEM. A, vol. 107, no. 41, 2003, pages 8659 - 8664
F. D. LEWISB. A. YOONT . ARAIT. IWASAKIK. TOKUMARU, J. AM. CHEM. SOC., vol. 117, no. 11, 1995, pages 3029 - 3036
HOBZA, Z ., HAVLAS, CHEM. REV., vol. 100, no. 11, 2000, pages 4253 - 4264
J. MOL. JOSEPHE. D. JEMIS, J. AM. CHEM. SOC., vol. 129, no. 15, 2007, pages 4620 - 4632
K. ARAIY. KOBAYASHIJ. ABE, CHEM. COMMUN., vol. 51, 2015, pages 3057 - 3060
ARAI, K. ET AL.: "Rational molecular designs for drastic acceleration of the color-fading speed of photochromic naphthopyrans", CHEMICAL COMMUNICATIONS, vol. 51, no. 15, 2015, pages 3057 - 3060, XP055544377, ISSN: 1359-7345
CHAMONTIN, K. ET AL.: "Synthesis and reactivity of formyl-substituted photochromic 3,3-Diphenyl-[3H]- naphtho[2,1-b]pyrans", TETRAHEDRON, vol. 55, no. 18, 30 April 1999 (1999-04-30), pages 5821 - 5830, XP004163608, ISSN: 0040-4020
OLIVEIRA, M. M. ET AL.: "Remarkable thermally stable open forms of photochromic new N- substituted benzopyranocarbazoles", JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A: CHEMISTRY, vol. 198, no. 2-3, 15 August 2008 (2008-08-15), pages 242 - 249, XP022710250, ISSN: 1010-6030
INAGAKI, Y. ET AL.: "A simple and versatile strategy for rapid color fading and intense coloration of photochromic naphthopyran families", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 139, no. 38, 13 September 2017 (2017-09-13), pages 13429 - 13441, XP055544381, ISSN: 0002-7863
Y.M. SHINOHARAT. ARAI, BULL. CHEM. SOC. JPN., vol. 81, no. 11, 2008, pages 1500 - 1504
Y.M. NORIKANEN., NAKAYAMAN., TAMAOKIT., ARAIU . NAGASHIMA, J. PHYS. CHEM. A, vol. 107, no. 41, 2003, pages 8659 - 8664
F. D. LEWISB. A. YOONT . ARAIT. IWASAKIK. TOKUMARU, J. AM. CHEM. SOC., vol. 117, no. 11, 1995, pages 3029 - 3036
HOBZA, Z ., HAVLAS, CHEM. REV., vol. 100, no. 11, 2000, pages 4253 - 4264
J. MOL. JOSEPHE. D. JEMIS, J. AM. CHEM. SOC., vol. 129, no. 15, 2007, pages 4620 - 4632
K. ARAIY. KOBAYASHIJ. ABE, CHEM. COMMUN., vol. 51, 2015, pages 3057 - 3060
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