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Synlett
Volumn , Issue 17, 2008, Pages 2633-2636
The synthesis of triazadibenzol[cd,g]azulenes: How to connect four different rings in just one step?
Author keywords

Electrocyclic reactions; Fused ring systems; Oxidations; Pyridines; Quantum chemical calculations
Indexed keywords

6 METHYL 4H IMIDAZO (1,2 A) PYRIDINE DERIVATIVE; AZULENE DERIVATIVE; METHYL GROUP; PYRIDINE DERIVATIVE; TETRACYCLINE; TRIAZODIBENZO [CD,G] AZULENE DERIVATIVE; UNCLASSIFIED DRUG;
EID: 55449120455     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0028-1083496     Document Type: Article
Times cited : (8)
References (23)
  • 15
    • 55449131252 scopus 로고    scopus 로고
    • Crystal Data for Compound 10: C44H34N 3CHCl3, Mr, 913.53 gmol-1, blue prism, size 0.04 × 0.04 × 0.04 mm3, triclinic, space group Pi, a, 11.4589 (4, b, 12.5571 (5, c, 15.8154 (9) Å, α, 82.756 (2)°, β, 68.797 (3)°, γ, 79.149 (2)°, V, 2079.51 (16) Å3, T, 90 °C, Z, 2, pcalcd, 1.459 gem -3, μ(Mo-Kα, 4.59 cm-1, F(000, 940, 14823 reflections in h(-14/14, k(-16/16, 1(-16/20, measured in the range 1.95°≤ Θ ≤27.50°, completeness Θmax, 99.3, 9491 independent reflections, Rint, 0.0415, 6118 reflections with Fo >4σFo, 553 parameters, O restraints, R1obs, 0.0663, wR2obs, 0.1607, R1 all, 0.1129, wR2all, 0.1922, GOOF, 0.983, largest
    • 3. CCDC 686207 (10) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/ retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44 (1223)336033; or deposit@ccdc.cam.ac.uk].
  • 16
    • 55449129760 scopus 로고    scopus 로고
    • Preparation of 10 Starting from 1 and 2-Amino-6-methylpyridine (6; R, Me, Typical Procedure: A solution of 2-amino-6-methylpyridine (6; 0.216 g, 2.00 mmol) in MeCN (20 mL) was added to a solution of oxalic acid bisimidoylchloride 1 (0.610 g, 2.00 mmol) in MeCN (20 mL, After addition of Et3N (1.4 mL, 10 mmol) the reaction mixture was heated under reflux for about 4-5 h. The purple solution was cooled to r.t, evaporated to dryness and the product was isolated by column chromatography (SiO2, toluene-acetone, 100:1, The bis(2,11,11b-triazadibenzo[cd,g] dihydroazulene) 10 was obtained as dark blue crystalline solid. Selected data for 10: yield: 0.20g, 30, mp >250 °C (dec, MS (DEI, mlz, 675 (5, M, 674 (8, M, 1, 541 (12, 486 (26, 441 (11, 338 (16, 337 (18, 234 (31, 205 (21, 149 (35, 133 (47, 106 (100, 78 (27, 1H NMR (CDCl3, δ, 2.17 (s, 6 H, 2.25 s, 6 H, 3.99
    • max (log ε) = 272 (4.4), 457 (3.9), 537 (4.0), 571 (3.9) nm.
  • 17
    • 55449134558 scopus 로고    scopus 로고
    • Frisch, M. J, Trucks, G. W, Schlegel, H. B, Scuseria, G. E, Robb, M. A, Cheeseman, J. R, Montgomery, J. A. Jr, Vreven, T, Kudin, K. N, Burant, J. C, Millam, J. M, Iyengar, S. S, Tomasi, J, Barone, V, Mennucci, B, Cossi, M, Scalmani, G, Rega, N, Petersson, G. A, Nakatsuji, H, Hada, M, Ehara, M, Toyota, K, Fukuda, R, Hasegawa, J, Ishida, M, Nakajima, T, Honda, Y, Kitao, O, Nakai, H, Klene, M, Li, X, Knox, J. E, Hratchian, H. P, Cross, J. B, Bakken, V, Adamo, C, Jaramillo, J, Gomperts, R, Stratmann, R. E, Yazyev, O, Austin, A. J, Cammi, R, Pomelli, C, Ochterski, J. W, Ayala, P. Y, Morokuma, K, Voth, G. A, Salvador, P, Dannenberg, J. J, Zakrzewski, V. G, Dapprich, S, Daniels, A. D, Strain, M. C, Farkas, O, Malick, D. K, Rabuck, A. D, Raghavachari, K, Foresman, J. B, Ortiz, J. V, Cui, Q, Baboul, A. G, Clifford, S, Cioslowski, J, Stefanov, B. B, Liu, G, Liashenko, A, Piskorz, P, Komaromi, I, Martin, R. L, Fox, D. J, Keith
    • (a) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A. Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford CT, 2004.
  • 18
    • 55449138306 scopus 로고    scopus 로고
    • Details of the quantum chemical calculations may be obtained from E.-U. Würthwein upon request
    • (b) Details of the quantum chemical calculations may be obtained from E.-U. Würthwein upon request.
  • 19
    • 0038617502 scopus 로고    scopus 로고
    • Energies of the DFT-optimized structures were calculated using the SCS-MP2-method. They include DFT zero point correction. See: Grimme, S
    • Energies of the DFT-optimized structures were calculated using the SCS-MP2-method. They include DFT zero point correction. See: Grimme, S. J. Chem. Phys. 2003, 118, 9095.
    • (2003) J. Chem. Phys , vol.118 , pp. 9095

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.