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Volumn , Issue 17, 2007, Pages 2733-2737

Electrocyclization reactions of annulated 1,2-diazahepta-2,4-dien-6-ynyl anions

Author keywords

6 azafulvenes; Anionic electrocyclic reactions; Heterocycles; Hydrazones; Indenes; Quinolines

Indexed keywords

1 (2 BUTYL 1H INDEN 1 YLIDENE) 2 PHENYLHYDRAZINE; 1 [2 (HEX 1 YNYL)BENZYLIDENE] 2 PHENYL HYDRAZINE; AZEPINE DERIVATIVE; HYDRAZONE DERIVATIVE; ISOQUINOLINE DERIVATIVE; N METHYL HYDRAZONE; UNCLASSIFIED DRUG;

EID: 35649016710     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-991071     Document Type: Article
Times cited : (8)

References (41)
  • 20
    • 35648954670 scopus 로고    scopus 로고
    • Preparation of 1-[2-(Hex-1-ynyl)benzylidene]-2-phenylhydrazine (12a, A mixture of 2-(1-hexynyl)benz-aldehyde (0.93 g, 5.00 mmol) and phenylhydrazine (0.54 g, 5.00 mmol) in anhyd CH2Cl2 (20 mL) was stirred in the presence of molecular sieves (4 Å) at r.t. for 16 h. Molecular sieves were removed by filtration through Celite and washed with CH2Cl2 (20 mL, The solvent was removed in vacuo to afford the hydrazone 12a (1.10 g, 4.00 mmol, 80, as a yellow oil. The obtained hydrazone was pure enough to be used without further purification. FTIR (film, 3313 (br, w, 2931 (s, 2871 (s, 2862 (m, 2225 (m, 1575 (m, 1494 (s, 1448 (m, 1257 (s, 1145 (m) cm-1. 1H NMR (400 MHz, CDCl 3, δ, 0.98 (t, J, 7.3 Hz, 3 H, 1.47-1.68 (m, 4 H, 2.48 (t, J, 7.4 Hz, 2 H, 6.87 (tt, J, 7.3, 1.2 Hz, 1 H, 7.11-7.14 (m, 2 H, 7.19 (dd, J, 7.4, 1.4 Hz, 1 H, 7.25-7.30 m, 3 H
    • 2: C, 82.57; H, 7.29; N, 10.14. Found: C, 82.87; H, 7.48; N, 9.57.
  • 21
    • 35649009960 scopus 로고    scopus 로고
    • Preparation of 1-(2-Butyl-1H-inden-1-ylidene)-2- phenylhydrazine (13a, Hydrazone 12a (0.28 g, 1.00 mmol) was added under argon to the solution of t-BuOK (0.22 g, 2.00 mmol) in DMF (5 mL) and the mixture was stirred at 50°C until all starting hydrazone had disappeared (approx. 5 h, TLC monitoring, H2O (20 mL) was added and the mixture was extracted with Et2O (3 x 20 mL, The combined organic extracts were dried with MgSO4 and the residue was purified by flash chromatography (Et2O-pentane-Et3N, 0.5:10:0.2) giving 13a (0.07 g, 0.25 mmol, 25, as a yellowish oil. FTIR (film, 2956 (s, 2927 (s, 1600 (s, 1566 (s, 1504 (s, 1494 (s, 1255 (s, 1207 (s, 1168 (s, 1151 (w, 1122 (m, 1093 (w) cm-1. 1H NMR (500 MHz, CDCl3, δ, 1.00 (t, J, 7.1 Hz, 3 H, 1.43-1.52 (m, 2 H, 1.68-1.75 (m, 2 H, 2.66-2.69 (m, 2 H, 6.56 (s, 1 H, 7.03 tt, J
    • 2: C, 82.57; H, 7.29; N, 10.14. Found: C, 82.64; H, 7.54; N, 9.62.
  • 22
    • 35648950547 scopus 로고    scopus 로고
    • 2(OH). These data can be obtained free of charge at 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, E-mail: deposit@ccdc.cam.ac.uk].
    • 2(OH). These data can be obtained free of charge at 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, E-mail: deposit@ccdc.cam.ac.uk].
  • 23
    • 35649010457 scopus 로고    scopus 로고
    • 4 and the residue was purified by flash chromatography (tert-butyl methyl ether) giving 15 (0.09 g, 0.47 mmol, 47%) as a yellow oil. All spectroscopic and physical data were in accordance with published data (see ref. 11).
    • 4 and the residue was purified by flash chromatography (tert-butyl methyl ether) giving 15 (0.09 g, 0.47 mmol, 47%) as a yellow oil. All spectroscopic and physical data were in accordance with published data (see ref. 11).
  • 28
    • 0038798495 scopus 로고    scopus 로고
    • Bühl, M.; Schaefer, H. F. III J. Am. Chem. Soc. 1993, 115, 9143.
    • (b) Bühl, M.; Schaefer, H. F. III J. Am. Chem. Soc. 1993, 115, 9143.
  • 39
    • 35648945346 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.
  • 40
    • 35648949459 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.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.