메뉴 건너뛰기
Synlett
Volumn , Issue 6, 2007, Pages 913-916
Synthesis and characterization of acetylenic scaffolds containing dithiafulvenes about a central anthraquinodimethane core
Author keywords

Alkynes; Chromophores; Conjugation; Halides; Heterocycles
Indexed keywords

ACETYLENE DERIVATIVE; ALKENE DERIVATIVE; ALKYNE DERIVATIVE; ANTHRAQUINODIMETHANE; DITHIAFULVENE DERIVATIVE; HALIDE; METHANE; TETRATHIAFULVALENE; UNCLASSIFIED DRUG;
EID: 34247094703     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-973874     Document Type: Article
Times cited : (9)
References (18)
  • 11
    • 34247144351 scopus 로고    scopus 로고
    • Synthesis of 2b Compounds 4 (80 mg, 0.14 mmol) and 1 (2.8 g, 8.5 mmol) were dissolved in THF (40 mL) and MeOH (120 mL, Then, K 2CO3 (1.41 g, 10.2 mmol) was added to the solution that was stirred for 45 min until TLC showed complete deprotection of both compounds. The mixture was diluted with Et2O (100 mL) and washed with H 2O (2 x 150 mL, The organic phase was dried (MgSO4) and concentrated in vacuo. The residue was dissolved in CH2Cl2 (100 mL, whereupon Hay catalyst (8 mL) was added [Hay catalyst: CuCl (0.52 g, 5.2 mmol, TMEDA (0.64 mL, 5.6 mmol, CH2Cl2 (9 mL, The mixture was vigorously stirred under open atmosphere until TLC showed no remaining starting materials. Repeated flash chromatography (SiO2, CH2Cl2 → CH2Cl2-EtOAc, 9:1) yielded almost pure 2b (63 mg) that was recrystallized from CH
    • 8: C, 58.35; H, 2.75. Found: C, 58.17; H, 2.89.
  • 13
    • 34247134182 scopus 로고    scopus 로고
    • Synthesis of 5 NCS (528 mg, 3.95 mmol) was dissolved in anhyd acetone (10 mL) under an argon atmosphere, whereupon a solution of NaI (600 mg, 4.00 mmol) in anhyd acetone (5 mL) was slowly added, resulting in the formation of a precipitate. After stirring for 15 min at r.t, a mixture of 1 (330 mg, 1.01 mmol) and AgNO3 (10 mg, 0.059 mmol) in anhyd acetone (5 mL) was added. The reaction mixture was left in the dark at r.t. overnight. Then it was cooled on an ice bath, and H2O (30 mL) was added. The resulting red precipitate was isolated and then redissolved in CH2Cl 2 (15 mL, The solution was dried (MgSO4, filtered, and concentrated in vacuo. Purification by flash chromatography (SiO2, CH2Cl2-cyclohexane, 1:1) gave 5 as an orange solid (320 mg, 83, mp 73°C (decomp, 1H NMR (300 MHz, CDCl 3, δ, 5.29 (s, 6 H, 6.49 s, 1 H, 13C NMR
    • +].
  • 15
    • 34247101339 scopus 로고    scopus 로고
    • Synthesis of 6 Method 1: LiI (6.4 mg, 0.046 mmol, 1,2,2,6,6-penta-methylpiperidine (0.12 mL, 0.66 mmol, Pd2(dba) 3, 6.0 mg, 0.008 mmol) were dissolved in deoxygenated benzene (4 mL) under an argon atmosphere. Then, CuI (1.3 mg, 0.006 mmol) and trimethylsilylacetylene (0.02 mL, 0.15 mmol) were added. A solution of the iodide 5 (42 mg, 0.11 mmol) in benzene (4 mL) was added, and the mixture was heated at 30°C for 24 h. The crude mixture was filtered through a short plug of silica (SiO2, CH2Cl2, affording the product 6 as a yellow solid that slowly turned black upon standing (23 mg, 59, Method 2: Compound 1 (0.25 g, 0.76 mmol) was deprotected by K2CO3 in MeOH-THF as described previously (ref. 3, The resulting terminal acetylene was dissolved in CH2Cl2 (30 mL, whereupon trimethylsilyl-acetylene (1.0 mL, 7.0 mmol) was added followed by Hay cataly
    • +].
  • 16
    • 34247169780 scopus 로고    scopus 로고
    • Synthesis of 7 Compound 6 (83 mg, 0.24 mmol) was dissolved in THF (3.5 mL) and MeOH (10 mL, whereupon K2CO3 (0.10 g, 8 mmol) was added. After stirring for 1 h, the deprotection was complete (according to TLC analysis, and Et2O (100 mL) was added. The organic phase was extracted with H2O (75 mL, dried (MgSO4, and concentrated in vacuo. The residue was dissolved in CH2Cl2 (30 mL) and Hay catalyst (1 mL) was added [Hay catalyst: CuCl (0.13 g, 1.3 mmol, TMEDA (0.16 g, 1.4 mmol, CH2Cl2 (4.5 mL, The reaction mixture was stirred for 1 h under open atmosphere and then concentrated in vacuo. Column chromatography (SiO2, CH2Cl 2-cyclohexane, 1:1) followed by recrystallization from CH 2Cl2-MeOH gave pure 7 (43 mg, 64, mp 153°C (decomp, 1H NMR (300 MHz, CDCl3, δ, 3.85 (s, 6 H, 3.87 s
    • 4: C, 51.60; H, 2.53; found: C, 51.64; H, 2.53.
  • 17
    • 34247165619 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, 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-Lah
    • 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.; 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 B.03; Gaussian, Inc.: Pittsburgh PA, 2003.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.