Gold-catalyzed oxycyclization of allenic carbamates: expeditious synthesis of 1,3-oxazin-2-ones

被引:31
作者
Alcaide, Benito [1 ]
Almendros, Pedro [2 ]
Teresa Quiros, M. [1 ]
Fernandez, Israel [3 ]
机构
[1] Univ Complutense Madrid, Fac Quim, CSIC,Dept Quim Organ 1, Unidad Asociada,Grp Lactamas & Heterociclos Bioac, E-28040 Madrid, Spain
[2] CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
[3] Univ Complutense Madrid, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
关键词
allenes; computational chemistry; gold; gold catalysis; heterocycles; reaction mechanisms; THERMODYNAMICALLY FAVORED ISOMERS; TERT-BUTYL CARBONATES; HYBRID MOLECULES; CYCLIZATION; ISOMERIZATION; PRODUCT; ALKYNES; ACCESS; SEMISYNTHESIS; DERIVATIVES;
D O I
10.3762/bjoc.9.93
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A combined experimental and computational study on regioselective gold-catalyzed synthetic routes to 1,3-oxazinan-2-ones (kinetically controlled products) and 1,3-oxazin-2-one derivatives (thermodynamically favored) from easily accessible allenic carbamates has been carried out.
引用
收藏
页码:818 / 826
页数:9
相关论文
共 76 条
[1]   The allenic Pauson-Khand reaction in synthesis [J].
Alcaide, B ;
Almendros, P .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (16) :3377-3383
[2]   Exploiting [2+2] cycloaddition chemistry: achievements with allenes [J].
Alcaide, Benito ;
Almendros, Pedro ;
Aragoncillo, Cristina .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) :783-816
[3]   Gold-catalysed tuning of reactivity in allenes: 9-endo hydroarylation versus formal 5-exo hydroalkylation [J].
Alcaide, Benito ;
Almendros, Pedro ;
Cembellin, Sara ;
Martinez del Campo, Teresa ;
Fernandez, Israel .
CHEMICAL COMMUNICATIONS, 2013, 49 (13) :1282-1284
[4]   Unveiling the Reactivity of Propargylic Hydroperoxides under Gold Catalysis [J].
Alcaide, Benito ;
Almendros, Pedro ;
Teresa Quiros, M. ;
Lopez, Ramon ;
Menendez, Maria I. ;
Sochacka-Cwikla, Aleksandra .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (02) :898-905
[5]   Scandium-Catalyzed Preparation of Cytotoxic 3-Functionalized Quinolin-2-ones: Regioselective Ring Enlargement of Isatins or Imino Isatins [J].
Alcaide, Benito ;
Almendros, Pedro ;
Aragoncillo, Cristina ;
Gomez-Campillos, Gonzalo ;
Arno, Manuel ;
Domingo, Luis R. .
CHEMPLUSCHEM, 2012, 77 (07) :563-569
[6]   Palladium-catalyzed carbocyclization-cross-coupling reactions of two different allenic moieties: synthesis of 3-(buta-1,3-dienyl) carbazoles and mechanistic insights [J].
Alcaide, Benito ;
Almendros, Pedro ;
Alonso, Jose M. ;
Fernandez, Israel .
CHEMICAL COMMUNICATIONS, 2012, 48 (52) :6604-6606
[7]   Allenyl-β-lactams: versatile scaffolds for the synthesis of heterocycles [J].
Alcaide, Benito ;
Almendros, Pedro .
CHEMICAL RECORD, 2011, 11 (06) :311-330
[8]   Novel Cyclization Reactions of Aminoallenes [J].
Alcaide, Benito ;
Almendros, Pedro .
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (14-15) :2561-2576
[9]   Gold- or Palladium-Catalyzed Allene Carbocyclization/Functionalization: Simple and Efficient Synthesis of Carbazoles [J].
Alcaide, Benito ;
Almendros, Pedro ;
Alonso, Jose M. ;
Teresa Quiros, M. ;
Gadzinski, Pawel .
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (11-12) :1871-1876
[10]   Gold catalyzed oxycyclizations of alkynols and alkyndiols [J].
Alcaide, Benito ;
Almendros, Pedro ;
Miguel Alonso, Jose .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (12) :4405-4416