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Synlett
Volumn , Issue 10, 2008, Pages 1515-1519
Facile and selective synthesis of propargylic amines and 1,6-diynes: One-pot three-component coupling reactions of alkynylsilanes, aldehydes and amines by a cooperative catalytic system comprised of CuCl and Cu(OTF) 2
Author keywords

1,6 diyne; Alkynylsilane; Copper catalyst; Multicomponent coupling reaction; Propargylic amine
Indexed keywords

ALDEHYDE DERIVATIVE; ALKYNE DERIVATIVE; ALKYNYL GROUP; AMINE; COPPER CHLORIDE; SILANE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID;
EID: 46449121824     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/S-2008-1077790     Document Type: Article
Times cited : (24)
References (42)
  • 1
    • 0004180584 scopus 로고
    • Glasby, J. S, Ed, Plenum Press: New York
    • In Encyclopedia of the Alkaloids; Glasby, J. S., Ed.; Plenum Press: New York, 1975.
    • (1975) Encyclopedia of the Alkaloids
  • 21
    • 33745190269 scopus 로고    scopus 로고
    • For selected papers for the reactions using an alkynylsilane, see: a
    • For selected papers for the reactions using an alkynylsilane, see: (a) Yadav, J. S.; Raju, A. K.; Sunitha, V. Tetrahedron Lett. 2006, 47, 5269.
    • (2006) Tetrahedron Lett , vol.47 , pp. 5269
    • Yadav, J.S.1    Raju, A.K.2    Sunitha, V.3
  • 30
    • 46449122749 scopus 로고    scopus 로고
    • General Procedure for the Synthesis of a Propargyl Amine: To a MeCN solution (300 μL) in a screw-capped vial under an N2 atmosphere, alkynylsilane 1 (0.45 mmol, aldehyde 2 (0.30 mmol, amine 3 (0.36 mmol, Cu(OTf)2 (5.4 mg, 0.015 mmol) and CuCl (1.5 mg, 0.015 mmol) were successively added, and the vial was sealed with a cap containing a PTFE septum. The reaction mixture was heated at 100 °C until the reaction was completed as monitored by TLC. After the reaction, the mixture was directly subjected to SiO2 gel without the usual extraction, and was purified by flash column chromatography (hexane-EtOAc) to give the corresponding propargyl amines in the yields shown in Table 2. 1-[1-(4-Methoxyphenyl)-3- phenylpropyn-2-yl]-4-methyl-piperazine (13, pale yellow oil. 1H NMR (500 MHz, CDC13, δ, 2.21 (s, 3 H, 2.40 (m, 4 H, 2.59 (m, 4 H, 3.74 (s, 3 H, 4.69 (s, 1 H, 6.82 (d, J, 7.5 Hz, 2 H, 7.23 m, 3 H
    • 23NO: 293.1780; found: 293.1785.
  • 31
    • 46449131936 scopus 로고    scopus 로고
    • similar coupling reaction was carried
    • a out with phenylacetylene, propargylic amine was obtained in a 61% yield 7 h
    • When a similar coupling reaction was carried out with phenylacetylene, propargylic amine 4 was obtained in a 61% yield (7 h).
    • , vol.4
    • When1
  • 34
    • 46449137210 scopus 로고    scopus 로고
    • General Procedure for the Synthesis of a Symmetrical 1,6-Diyne: To a MeCN solution (300 μL) in a screw-capped vial under a N2 atmosphere, alkynylsilane 1 (0.90 mmol, paraformaldehyde 2h (0.90 mmol, primary amine 3 (0.30 mmol, Cu(OTf)2 (5.4 mg, 0.015 mmol) and CuCl (1.5 mg, 0.015 mmol) were successively added, and the vial was sealed with a cap containing a PTFE septum. The reaction mixture was heated at 100 °C for 24 h. After the reaction, the mixture was directly subjected to SiO2 gel without the usual extraction, and was purified by flash column chromatography (hexane-EtOAc) to give the corresponding 1,6-diynes in the yields shown in Table 3. N-Benzyl-N, N-bis[3-(tert- butyldimethylsilyl)propyn-2-yl]amine (27, colorless oil. 1H NMR (500 MHz, CDCl3, δ, 0.12 (s, 12 H, 0.96 (s, 18 H, 3.40 (s, 4 H, 3.69 (s, 2 H, 7.32 (m, 5 H, 13C NMR 12
    • 2: 412.2856; found: 412.2866.
  • 41
    • 46449136902 scopus 로고    scopus 로고
    • Procedure for the Synthesis of 1-Aminoindolizine 9′: To a MeCN solution (300 μL) in a screw-capped vial under a N2 atmosphere, alkynylsilane 1a (78 mg, 0.45 mmol, aldehyde 2g (48 mg, 0.45 mmol, amine 3a (26 mg, 0.30 mmol) and Cu(OTf)2 (5.4 mg, 0.015 mmol) were successively added, and the vial was sealed with a cap containing a PTFE septum. The reaction mixture was heated at 100 °C for 1 h. After the reaction, the mixture was directly subjected to Al2O 3 gel without the usual extraction, and was purified by flash column chromatography (hexane, EtOAc) to give 1-aminoindolizine 9′ in 97% yield (80 mg, 3-Phenyl-1-piperidin-1-ylindolizine (9′, yellow oil. 1H NMR (500 MHz, CDC13, δ, 1.50 (quint, J, 6.0 Hz, 2 H, 1.71 (quint, J, 6.0 Hz, 4 H, 2.94 (t, J, 6.0 Hz, 4 H, 6.30 (t, J, 7.5 Hz, 1 H, 6.44 t, J, 7.5
    • 3): δ = 24.4, 26.5, 55.2, 105.7, 110.7, 114.3, 118.1, 121.6, 126.7, 127.5, 127.7, 128.6, 128.9, 131.1, 132.6.MS(EI): m/z = 276.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.