{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2024,9,16]],"date-time":"2024-09-16T15:28:20Z","timestamp":1726500500834},"reference-count":19,"publisher":"CLOCKSS Archive","issue":"12","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["HETEROCYCLES"],"published-print":{"date-parts":[[2002]]},"DOI":"10.3987\/com-02-9612","type":"journal-article","created":{"date-parts":[[2009,3,9]],"date-time":"2009-03-09T04:01:45Z","timestamp":1236571305000},"page":"2227","source":"Crossref","is-referenced-by-count":3,"title":["Synthesis of New Thiopyrylocyanines Incorporated Thiopyrano[2,3-b]indole Ring as the Main Constituent"],"prefix":"10.13030","volume":"57","author":[{"given":"Yoshinori","family":"Tominaga","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yasuhiro","family":"Shigemitsu","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Shun-ichi","family":"Hirayama","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"5187","reference":[{"key":"#cr-split#-10.3987\/COM-02-9612-1.1","unstructured":"a) A. T. Petera and H. S. Freeman, \u201cColour Chemistry: The Design and Synthesis of Organic Dyes and Pigments,\u201d Advances in Colour Chemistry Series, Elsevier Applied Science, New York, 1991;"},{"key":"#cr-split#-10.3987\/COM-02-9612-1.2","unstructured":"b) D. R. Waring and G. Halls, \u201cThe Chemistry and Application of Dyes,\u201d Plenum Press, New York, 1991;"},{"key":"#cr-split#-10.3987\/COM-02-9612-1.3","doi-asserted-by":"crossref","unstructured":"c) J. Fabian, H. Nakazumi, and M. Matsuoka, Chem. Rev., 1992, 92, 1197;","DOI":"10.1021\/cr00014a003"},{"key":"#cr-split#-10.3987\/COM-02-9612-1.4","unstructured":"d) S. G. R. Guinot, J. D. Hepworth, and M. Wainwright, J. Chem. Soc., Perkin Trans. 2, 1998, 2972; d) Y. Matsuda, K. Katou, H. Matsumoto, S. Ide, K. Takahashi, K. Torisu, K. Furuno, and S. Maeda, Yakugaku Zasshi, 1992, 112, 42 and references cited therein."},{"key":"10.3987\/COM-02-9612-2","doi-asserted-by":"crossref","unstructured":"2. C. Kanony, B. Akerman, and E. M. Tuite, J. Am. Chem. Soc., 2001, 123, 7985.","DOI":"10.1021\/ja001047n"},{"key":"#cr-split#-10.3987\/COM-02-9612-3.1","doi-asserted-by":"crossref","unstructured":"a) M. Mizoguchi, M. Ishiyama, M. Shiga, and K. Sasamoto, Bunseki Kagaku, 1996, 45, 111;","DOI":"10.2116\/bunsekikagaku.45.111"},{"key":"#cr-split#-10.3987\/COM-02-9612-3.2","doi-asserted-by":"crossref","unstructured":"b) M. Mizoguchi, M. Shiga, and K. Sasamoto, Chem. Pharm. Bull., 1993, 41, 620;","DOI":"10.1248\/cpb.41.620"},{"key":"#cr-split#-10.3987\/COM-02-9612-3.3","unstructured":"c) K. L. Cheng, K. Ueno, and T. Imamura, \u201cHandbook of Organic Analytical Reagents,\u201d CRC Press, Inc., Boca Raton, p. 267, 1982."},{"key":"#cr-split#-10.3987\/COM-02-9612-4.1","doi-asserted-by":"crossref","unstructured":"a) Y. Tominaga, K. Komiya, S. Itonaga, N. Yoshioka, S. Kataoka, K. Sasaki, and T. Hirota, Heterocycles, 1997, 46, 41;","DOI":"10.3987\/COM-97-S12"},{"key":"#cr-split#-10.3987\/COM-02-9612-4.2","doi-asserted-by":"crossref","unstructured":"b) Y. Tominaga, S. Itonaga, T. Kouno, and Y. Shigemitsu, Heterocycles, 2001, 55, 1447.","DOI":"10.3987\/COM-01-9260"},{"key":"10.3987\/COM-02-9612-5","doi-asserted-by":"crossref","unstructured":"5. Y. Tominaga, R.Natsuki, Y. Matsuda, and G. Kobayashi, Chem. Pharm. Bull., 1973, 21, 2770.","DOI":"10.1248\/cpb.21.2770"},{"key":"10.3987\/COM-02-9612-6","unstructured":"6. Though the stereochemistry of the products has not been decided, the structures shown in the figure have been estimated from the NMR spectra and the result of calculation by MOPAC."},{"key":"10.3987\/COM-02-9612-7","unstructured":"7. 4: Dark violet leaflets, mp 312-315 \u00b0C (DMF). 1H-NMR (DMSO-d6) \u03b4: 3.29 (6H, s, 2xNMe), 3.81 (6H, s, 2 x OMe), 3.86 (6H, s, 2 x OMe), 6.30 (2H, s, C=H), 7.14 (2H, dd, J=7.4, 8.2 Hz, 7, 7\u2019-H), 7.35 (2H, dd, J=7.4, 8.0 Hz, 8, 8\u2019-H), 7.66 (2H, d, J=8.0 Hz, 9, 9\u2019-H), 7.76 (2H, d, J=8.2 Hz, 6, 6\u2019-H). MS m\/z: 656 (M+)."},{"key":"10.3987\/COM-02-9612-8","unstructured":"8. 5: Red leaflets, mp 231-234 \u00b0C (MeOH). 1H-NMR (CDCl3 + CF3COOD) \u03b4: 3.17 (3H, s, Me), 4.13 (3H, s, NMe), 4.14 (3H, s, OMe), (3H, s, OMe), 7.77 (1H, t, J=8.2 Hz, 7-H), 7.89 (1H, d, J=8.2 Hz, 8-H), 7.96 (1H, t, J=8.2 Hz, 9-H), 8.45 (1H, d, J=8.2 Hz, 6-H)."},{"key":"10.3987\/COM-02-9612-9","unstructured":"9. 6: Greenish yellow needles, mp 275-278\u00b0C (MeOH). 1H-NMR (CDCl3) \u03b4: 3.74 (3H, s. NMe), 3.91 (3H, s, OMe), 3.97 (3H, s, OMe), 5.03 (1H, s, C=H), 5.76 (1H, s, C=H), 7.19-7.37 (3H, m, 6, 7, 8-H), 7.90 (1H, d, J=7.4 Hz, 9-H). MS m\/z: 329 (M+, 100)."},{"key":"10.3987\/COM-02-9612-10","unstructured":"10. 8a: Black crystals, mp 230 \u00b0C (decomp) (MeOH). Ms m\/z: 462 (M+). 8b: balck crystals, mp 240 \u00b0C (decomp), Ms m\/z : 489 (M+). 8c: black crystals, mp 230-240 \u00b0C (decomp) (MeOH), FAB MS:487 (M++1)."},{"key":"10.3987\/COM-02-9612-11","unstructured":"11. 10: Dark violet leaflets, mp 216-218 \u00b0C (MeOH), 1H-NMR (CDCl3) \u03b4: 3.88 (3H, s, NMe), 3.97 (3H, s, OMe), 4.04 (3H, s, OMe), 6.30 (1H, d, J=12.4 Hz, C=H), 7.22-7.44 (3H, m, 7, 8, 9-H), 7.74 (1H, d, J=8.2 Hz, 6-H), 8.24 (1H, d, J=12.4 Hz, C=H)."},{"key":"10.3987\/COM-02-9612-12","unstructured":"12. 11: Black crystals, mp 210-232 \u00b0C (CH2Cl2), 1H-NMR (CDCl3) \u03b4: 3.77 (3H, s, NMe), 4.03 (3H, s, OMe), 4.07 (3H, s, OMe), 6.40 (1H, s, C=H), 7.09-7.61 (4H, m, 6, 7, 8, 9-H), MS m\/z: 430 (M+)."},{"key":"10.3987\/COM-02-9612-13","unstructured":"13. 12: Black crystals, mp 230-232 \u00b0C (MeOH), 1H-NMR (CDCl3) \u03b4: 3.14 (3H, s, NMe), 4.02 (3H, s, NMe), 4.03 (3H, s, OMe), 4.09 (3H, s, OMe), 6.64 (1H, s, C=H), 6.70 (1H, d, J=8.00 Hz, 6-H), 7.27-7.65 (3H, m, 7, 8, 9-H), MS:m\/z 464 (M+)."}],"container-title":["HETEROCYCLES"],"original-title":[],"language":"en","deposited":{"date-parts":[[2024,6,24]],"date-time":"2024-06-24T20:34:44Z","timestamp":1719261284000},"score":1,"resource":{"primary":{"URL":"https:\/\/triggered.stanford.clockss.org\/ServeContent?doi=10.3987%2Fcom-02-9612"},"secondary":[{"URL":"https:\/\/triggered.edinburgh.clockss.org\/ServeContent?doi=10.3987%2Fcom-02-9612","label":"edinburgh"}]},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2002]]},"references-count":19,"journal-issue":{"issue":"12","published-print":{"date-parts":[[2002]]}},"alternative-id":["COM-02-9612"],"URL":"https:\/\/doi.org\/10.3987\/com-02-9612","relation":{},"ISSN":["0385-5414"],"issn-type":[{"type":"print","value":"0385-5414"}],"subject":[],"published":{"date-parts":[[2002]]}}}