A facile preparation of tetralins from arene-1,4-diones using titanium(IV) chloride and triethylsilane

被引:11
作者
Li, Gang [1 ,2 ]
Xiao, Qiong [1 ,2 ]
Li, Chun [1 ,2 ]
Wang, Xiaojian [1 ,2 ]
Yin, Dali [1 ,2 ]
机构
[1] Peking Union Med Coll, Dept Med Chem,Inst Mat Med, Beijing Key Lab Act Subst Discovery & Drugabil, State Key Lab Bioact Subst & Funct Nat Med, Beijing 100050, Peoples R China
[2] Chinese Acad Med Sci, Beijing 100050, Peoples R China
关键词
Tetralin; Arene-1,4-dione; Intramolecular cyclization; Ionic hydrogenation; CONDENSED POLYNUCLEAR HYDROCARBONS; AROMATIC ALCOHOLS; CYCLODEHYDRATION; SELECTIVITY; CYCLIZATION; RECEPTOR;
D O I
10.1016/j.tetlet.2011.10.054
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile method for the synthesis of tetralins has been described which uses various substituted phenylpentane-1,4-diones as starting material with a combination of TiCl4/Et3SiH. The synthesis involves three reactions under mild conditions. A mechanism has been proposed for the reductive cyclization through ionic hydrogenation, and titanium(IV) chloride catalyzed cyclization. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6827 / 6830
页数:4
相关论文
共 12 条
[1]   Isomerization of unsaturated hydrocarbons [J].
Bergmann, E .
CHEMICAL REVIEWS, 1941, 29 (03) :529-551
[2]   The synthesis of condensed polynuclear hydrocarbons by the cyclodehydration of aromatic alcohols II The synthesis of ionenes [J].
Bogert, MT ;
Davidson, D ;
Apfelbaum, PM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1934, 56 :959-963
[3]   The synthesis of compounds related to the sterols, bile acids, and oestrus-producing hormones Part I 1 2-cyclopentenophenanthrene [J].
Cook, JW ;
Hewett, CL .
JOURNAL OF THE CHEMICAL SOCIETY, 1933, :1098-1111
[4]   Enhanced selectivity to decalin in naphthalene hydrogenation under supercritical carbon dioxide [J].
Hiyoshi, N ;
Miura, R ;
Rode, CV ;
Sato, O ;
Shirai, M .
CHEMISTRY LETTERS, 2005, 34 (03) :424-425
[5]  
Hook BB, 1996, J MED CHEM, V39, P4036
[6]   SURFACE-MEDIATED REACTIONS .6. EFFECTS OF SILICA-GEL AND ALUMINA ON ACID-CATALYZED REACTIONS [J].
KROPP, PJ ;
BRETON, GW ;
CRAIG, SL ;
CRAWFORD, SD ;
DURLAND, WF ;
JONES, JE ;
RALEIGH, JS .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (13) :4146-4152
[7]   HIGH-AFFINITY AND SELECTIVITY ON 5-HT(1A) RECEPTOR OF 1-ARYL-4-[1-TETRALIN)ALKYL]PIPERAZINES .2. [J].
PERRONE, R ;
BERARDI, F ;
COLABUFO, NA ;
LEOPOLDO, M ;
TORTORELLA, V ;
FIORENTINI, F ;
OLGIATI, V ;
GHIGLIERI, A ;
GOVONI, S .
JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (06) :942-949
[8]   The synthesis of condensed polynuclear hydrocarbons by the cyclodehydration of aromatic alcohols. III. The cyclization of some phenylated alcohols and related olefins [J].
Roblin, RO ;
Davidson, D ;
Bogert, MT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1935, 57 (01) :151-159
[9]   NONTRICYCLIC ANTIDEPRESSANT AGENTS DERIVED FROM CIS-1-AMINO-4-ARYLTETRALIN AND TRANS-1-AMINO-4-ARYLTETRALIN [J].
WELCH, WM ;
KRASKA, AR ;
SARGES, R ;
KOE, BK .
JOURNAL OF MEDICINAL CHEMISTRY, 1984, 27 (11) :1508-1515
[10]   SYNTHESIS AND PHARMACOLOGICAL EVALUATION OF 1-PHENYL-3-AMINO-1,2,3,4-TETRAHYDRONAPHTHALENES AS LIGANDS FOR A NOVEL RECEPTOR WITH SIGMA-LIKE NEUROMODULATORY ACTIVITY [J].
WYRICK, SD ;
BOOTH, RG ;
MYERS, AM ;
OWENS, CE ;
KULA, NS ;
BALDESSARINI, RJ ;
MCPHAIL, AT ;
MAILMAN, RB .
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (17) :2542-2551