{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,18]],"date-time":"2025-10-18T10:25:30Z","timestamp":1760783130043},"reference-count":9,"publisher":"CLOCKSS Archive","issue":"2","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["HETEROCYCLES"],"published-print":{"date-parts":[[2001]]},"DOI":"10.3987\/com-00-s(i)92","type":"journal-article","created":{"date-parts":[[2009,3,9]],"date-time":"2009-03-09T05:58:03Z","timestamp":1236578283000},"page":"611","source":"Crossref","is-referenced-by-count":19,"title":["1,3-Dipolar Cycloaddition of 1-Phenylpropa-1,2-diene with Pyridinium Dicyanomethylides: 1-Phenylpropa-1,2-diene as a Synthetic Equivalent of 1-Phenylpropyne"],"prefix":"10.13030","volume":"54","author":[{"given":"Kiyoshi","family":"Matsumoto","sequence":"first","affiliation":[]},{"given":"Naoki","family":"Tanaka","sequence":"additional","affiliation":[]},{"given":"Takane","family":"Uchida","sequence":"additional","affiliation":[]},{"given":"Yukio","family":"Ikemi","sequence":"additional","affiliation":[]},{"given":"Naoto","family":"Hayashi","sequence":"additional","affiliation":[]},{"given":"Kinuyo","family":"Aoyama","sequence":"additional","affiliation":[]},{"given":"Akikazu","family":"Kakehi","sequence":"additional","affiliation":[]}],"member":"5187","reference":[{"key":"10.3987\/COM-00-S(I)92-1","unstructured":"1. Reviews of indolizines: D. Leaver, in Rodd's Chemistry of Carbon Compounds, Elsevier, Amsterdam, 1987, Suppl. 2nd Ed. Vol. IVH, p. 33; W. Flitsch, in Comprehensive Heterocyclic Chemistry, ed. by A. R. Katritzky and C. W. Rees, Pergamon, Oxford, 1984, Vol. 4, p. 443; F. J. Swinbourne, J. H. Hunt, and G. Klinkert, Adv. Heterocycl. Chem., 1978, 23, 103; T. Uchida and K. Matsumoto, Synthesis, 1976, 209; K. Matsumoto, Yuki Gosei Kagaku Kyokaishi, 1974, 32, 731."},{"key":"10.3987\/COM-00-S(I)92-2","unstructured":"2. Review of cyclazines: Y. Matsuda and H. Gotou, Heterocycles, 1987, 26, 2757; W. Flitsch, in Comprehensive Heterocyclic Chemistry, Vol. 4, ed. by A. Katritzky and C. W. Rees, Pergamon Press, Oxford, 1984; S.-J. Lee and J. M. Cook, Heterocycles,1983, 20, 87; W. Flitsch and U. Kramer, Adv. Heterocyclic Chem., 1978, 22, 322; A. Taurin, Chem. Heterocyclic Compd., 1977, 30, 245; K. Matsumoto, T. Uchida, and J. Yamauchi, Yuki Gosei Kagaku Kyokaishi, 1977, 35, 739."},{"key":"10.3987\/COM-00-S(I)92-3","unstructured":"3. K. Matsumoto, T. Uchida, Y. Yagi, H. Tahara, and R. M. Acheson, Heterocycles, 1985, 23, 2041."},{"key":"10.3987\/COM-00-S(I)92-4","unstructured":"4. I. Zugravescu and M. Petrovanu, N-Ylide Chemistry, McGraw-Hill International, New York, 1976; G. Surpateanu, J. P. Catteau, P. Karafiloglu, and A. Lablanche, Tetrahedron, 1976, 32, 2647; H. Fujita, J. Yamauchi, K. Matsumoto, H. Ohya-Nishiguchi, and Y. Deguchi, J. Magn. Res., 1979, 35, 171."},{"key":"10.3987\/COM-00-S(I)92-5","doi-asserted-by":"crossref","unstructured":"5. Recent results from our laboratory: K. Matsumoto, R. Ohta, T. Uchida, H. Nishioka, M. Yoshida, and A. Kakehi, J. Heterocycl. Chem., 1997, 34, 203; K. Matsumoto, H. Katsura, T. Uchida, K. Aoyama, and T. Machiguchi, J. Chem. Soc., Perkin Trans. 1, 1996, 2599; K. Matsumoto, T. Uchida, Y. Ikemi, T. Tanaka, M. Asahi, T. Kato, and H. Konishi, Bull. Chem. Soc. Jpn, 1987, 60, 3645; K. Matsumoto, T. Uchida, K. Aoyama, M. Nishikawa, T. Kuroda, and T. Okamoto, J. Heterocycl. Chem., 1988, 25, 1793.","DOI":"10.1002\/jhet.5570250637"},{"key":"10.3987\/COM-00-S(I)92-6","doi-asserted-by":"crossref","unstructured":"6. J.-L. Moreau and M. Gaudemar, J. Organometal. Chem., 1976, 108, 159.","DOI":"10.1016\/S0022-328X(00)82136-1"},{"key":"10.3987\/COM-00-S(I)92-7","unstructured":"7. Selected physical and spectroscopic data for 3-cyano-2-methyl-1-phenylindolizine (4a): mp 102-103\u00b0C (ethanol); MS (m\/z) 232(M+), 217(M+-CH3); IR(KBr): 2202 cm-1. 1H-NMR(500 MHz, CDCl3) \u03b4 2.46(s, 3H, CH3), 6.77(dd, J = 7.0 and 7.9 Hz, 1H, H-6), 6.97(dd, J = 7.0 and 8.6 Hz, 1H, H-7), 7.3-7.5(m, 5H, Ph-H), 7.51(d, J = 8.6 Hz, 1H, H-8), 8.20(d, J = 7.9 Hz, 1H, H-5). 13C-NMR(125 MHz, CDCl3) \u03b4 11.0(CH3), 95.4(C-3), 112.8(CN), 114.1(C-6), 115.6(C-1), 117.7(C-7), 122.3(C-8), 125.1(C-5), 126.8(PhC-4\u2019), 128.7(PhC-2\u2019), 129.5(PhC-3\u2019), 132.3(C-2), 133.3(C-8a), 143.2(PhC-1\u2019). Anal. Calcd for C16H12N2: C, 82.73; H, 5.21; N, 12.06. Found: C, 82.77; H, 4.97; N, 11.94. 3-Cyano-1-methyl-2-phenylindolizine (5a): mp 167-169\u00b0C (ethanol); MS (m\/z) 232(M+); IR(KBr): 2194 cm-1. 1H-NMR(500 MHz, CDCl3) \u03b4 2.36(s, 3H, CH3), 6.80(dd, J = 6.7 Hz, 1H, H-6), 7.00(dd, J = 6.7 Hz, 1H, H-7), 7.4-7.6(m, 5H, Ph-H), 7.41(d, J = 6.7 Hz, 1H, H-8), 8.24(d, J = 6.7 Hz, 1H, H-5). 13C-NMR(125 MHz, CDCl3) \u03b4 9.2(CH3), 93.1(C-3), 109.2(C-1), 112.9(CN), 114.8(C-6), 117.8(C-7), 121.2(C-8), 125.2(C-5), 128.0(PhC-4\u2019), 128.7(PhC-2\u2019), 129.4(PhC-3\u2019), 132.4(C-2), 135.0(C-8a), 136.5(PhC-1\u2019). Anal. Calcd for C16H12N2: C, 82.73; H, 5.21; N, 12.06. Found: C, 82.60; H, 5.27; N, 11.97."},{"key":"10.3987\/COM-00-S(I)92-8","unstructured":"8. Crystal data for 4b: C17H14N2, M=246.31, dimensions 0.12 x 0.28 x 0.48 mm, monoclinic, space group = P21\/n, a = 10.624 (5), b = 7.458 (4), c = 34.304 (4) \u00c5, \u03b2 = 98.26 (2)\u00b0, U = 2689 (1) \u00c53, Z = 8, Dc= 1.216 gcm-3, \u03bc=0.76 cm-1, F(000)=1040. Data were collected on a Rigaku AFC5S difractometer using graphite-monochromated Mo-K\u03b1 radiation (\u03bb=0.71069 ). Of 6929 reflections which were collected, 6422 were unique (Rint=0.066). The structure was solved by direct methods and all non-hydrogen atoms were refined anisotropically using full-matrix least squares to give R=0.078, and Rw =0.142 for 1995 independent observed reflections with I >1.90\u03c3(I) and 343 variables for 2\u03b8max= 55.0\u00b0. 5b: C17H14N2, M=246.31, dimensions 0.34 x 0.54 x 0.96 mm, triclinic, space group = P1 , a = 11.296 (5), b = 13.616 (3), c = 9.924 (4) \u00c5, \u03b1 = 99.85 (5)\u00b0, \u03b2 = 98.26 (2)\u00b0, \u03b3 = 79.04 (3)\u00b0, U = 1355 (1) \u00c53, Z = 4, Dc= 1.207 gcm-3, \u03bc=0.72 cm-1, F(000)=520. Data were collected on a Rigaku AFC5S difractometer using graphite-monochromated Mo-K\u03b1 radiation (\u03bb=0.71069 ). Of 6531 reflections which were collected, 6217 were unique (Rint=0.023). The structure was solved by direct methods and all non-hydrogen atoms were refined anisotropically using full-matrix least squares to give R=0.095, and Rw=0.149 for 2562 independent observed reflections with I >1.90\u03c3(I) and 343 variables for 2\u03b8max= 55.0\u00b0."},{"key":"10.3987\/COM-00-S(I)92-9","unstructured":"9. The HOMO and LUMO energy levels of 1 and 2 were obtained using CAChe systems (Version 3.7, CAChe Scientific, Oxford Molecular Group; PM3 method: J. J. P. Stewart, J. Comp. Chem., 1989, 10, 209. (See Scheme 3)"}],"container-title":["HETEROCYCLES"],"original-title":[],"language":"en","deposited":{"date-parts":[[2024,6,24]],"date-time":"2024-06-24T20:32:24Z","timestamp":1719261144000},"score":1,"resource":{"primary":{"URL":"https:\/\/triggered.stanford.clockss.org\/ServeContent?doi=10.3987%2Fcom-00-s%28i%2992"},"secondary":[{"URL":"https:\/\/triggered.edinburgh.clockss.org\/ServeContent?doi=10.3987%2Fcom-00-s%28i%2992","label":"edinburgh"}]},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2001]]},"references-count":9,"journal-issue":{"issue":"2","published-print":{"date-parts":[[2001]]}},"alternative-id":["COM-00-S(I)92"],"URL":"https:\/\/doi.org\/10.3987\/com-00-s(i)92","relation":{},"ISSN":["0385-5414"],"issn-type":[{"type":"print","value":"0385-5414"}],"subject":[],"published":{"date-parts":[[2001]]}}}