Efficient One-Pot Synthesis of 2,2-Dimethyl-2H-chromenes via Pd(II)-Catalyzed Coupling and SiO2-Promoted Condensation of o-Halophenols with 2-Methyl-3-buten-2-ol

被引:2
作者
Tee, Jia Ti [1 ]
Yaeghoobi, Marzieh [1 ]
Chee, Chin Fei [1 ]
Rahman, Noorsaadah Abd. [1 ]
机构
[1] Univ Malaya, Dept Chem, Kuala Lumpur 50603, Malaysia
关键词
2,2-Dimethyl-2H-chromene; 2-methyl-3-buten-2-ol; palladium; phenol; REGIOSELECTIVE SYNTHESIS; 2H-1-BENZOPYRANS; BENZOPYRANS; DERIVATIVES; CYCLIZATION; PRECOCENES; CHROMENES; PHENOLS;
D O I
10.1080/00397911.2015.1056371
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient synthesis of 2,2-dimethyl-2H-chromenes was accomplished by Pd(II)-catalyzed coupling and SiO2-promoted condensation of o-halophenols with 2-methyl-3-buten-2-ol (1,1-dimethylallyl alcohol) in one pot. The method is very general and can be useful for the synthesis of some natural 2,2-dimethyl-2H-chromenes.
引用
收藏
页码:1920 / 1927
页数:8
相关论文
共 36 条
  • [1] Direct, regioselective synthesis of 2,2-dimethyl-2H-chromenes. Total syntheses of octandrenolone and precocenes I and II
    Adler, Marc J.
    Baldwin, Steven W.
    [J]. TETRAHEDRON LETTERS, 2009, 50 (36) : 5075 - 5079
  • [2] Microwave-assisted palladium mediated decarbonylation reaction: synthesis of eulatachromene
    Akanksha
    Maiti, Debabrata
    [J]. GREEN CHEMISTRY, 2012, 14 (08) : 2314 - 2320
  • [3] SYNTHESIS AND ANTIHYPERTENSIVE ACTIVITY OF 4-(1,2-DIHYDRO-2-OXO-1-PYRIDYL)-2H-1-BENZOPYRANS AND RELATED-COMPOUNDS, NEW POTASSIUM CHANNEL ACTIVATORS
    BERGMANN, R
    GERICKE, R
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (02) : 492 - 504
  • [4] Zeolite-induced heterodomino reaction. Regioselective synthesis of 2H-1-benzopyrans from phenols and alpha-alkynols
    Bigi, F
    Carloni, S
    Maggi, R
    Muchetti, C
    Sartori, G
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20) : 7024 - 7027
  • [5] Thieme Chemistry Journal Awardees - Where Are They Now? Microwave-Assisted Rhodium-Catalyzed Decarbonylation of Functionalized 3-Formyl-2H-chromenes: A Sequence for Functionalized Chromenes like Deoxycordiachromene
    Broehmer, Manuel C.
    Volz, Nicole
    Braese, Stefan
    [J]. SYNLETT, 2009, (09) : 1383 - 1386
  • [6] Chauder BA, 1998, SYNTHESIS-STUTTGART, P279
  • [7] Preparation of some 6-substituted 2,2-dimethyl- and 2,2- and 2,4-diphenyl-naphtho[1,2-b]pyrans
    Cotterill, WD
    Iqbal, M
    Livingstone, R
    [J]. JOURNAL OF CHEMICAL RESEARCH-S, 1998, (01): : 2 - 3
  • [8] Solvent-free synthesis of naphthopyrans under ball-milling conditions
    Dong, Ya-Wei
    Wang, Guan-Wu
    Wang, Lei
    [J]. TETRAHEDRON, 2008, 64 (44) : 10148 - 10154
  • [9] Ellis G. P., 1977, CHROMENES CHROMANONE
  • [10] Observations on the synthesis of photochromic naphthopyrans
    Gabbutt, CD
    Heron, BM
    Instone, AC
    Thomas, DA
    Partington, SM
    Hursthouse, MB
    Gelbrich, T
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (07) : 1220 - 1230