An umpolung strategy for intermolecular [2+2+1] cycloaddition of aryl aldehydes and nitriles: a facile access to 2,4,5-trisubstituted oxazoles

被引:2
作者
Basavaiah, Deevi [1 ]
Golime, Gangadhararao [1 ]
Banoth, Shivalal [1 ]
Todeti, Saidulu [1 ]
机构
[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, India
关键词
BAYLIS-HILLMAN REACTION; PAUSON-KHAND; CARBONYLATIVE CYCLOADDITION; ALKYNES; 1,3-DITHIANES; ANNULATION; REACTIVITY; CHEMISTRY;
D O I
10.1039/d2sc00046f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We have described the first example of an umpolung strategy for intermolecular [2 + 2 + 1] cycloaddition between two aryl aldehydes and a nitrile under the influence of TMSOTf that proceeds through the formation of N-C, O-C and C-C bonds providing a simple synthetic protocol for obtaining 2,4,5-trisubstituted oxazoles.
引用
收藏
页码:8080 / 8087
页数:8
相关论文
共 63 条
[1]  
[Anonymous], SCI SYNTHESIS HOUBEN
[2]   Recent advances in the Baylis-Hillman reaction and applications [J].
Basavaiah, D ;
Rao, AJ ;
Satyanarayana, T .
CHEMICAL REVIEWS, 2003, 103 (03) :811-891
[3]   The Baylis-Hillman reaction: a new continent in organic chemistry - our philosophy, vision and over three decades of research [J].
Basavaiah, Deevi ;
Naganaboina, Ram Tilak .
NEW JOURNAL OF CHEMISTRY, 2018, 42 (17) :14036-14066
[4]   Recent Contributions from the Baylis-Hillman Reaction to Organic Chemistry [J].
Basavaiah, Deevi ;
Reddy, Bhavanam Sekhara ;
Badsara, Satpal Singh .
CHEMICAL REVIEWS, 2010, 110 (09) :5447-5674
[5]   The Pauson-Khand reaction, a powerful synthetic tool for the synthesis of complex molecules [J].
Blanco-Urgoiti, J ;
Añorbe, L ;
Pérez-Serrano, L ;
Domínguez, G ;
Pérez-Castells, J .
CHEMICAL SOCIETY REVIEWS, 2004, 33 (01) :32-42
[6]   Recent Contributions to Hetero Diels-Alder Reactions [J].
Blond, Gaelle ;
Gulea, Mihaela ;
Mamane, Victor .
CURRENT ORGANIC CHEMISTRY, 2016, 20 (21) :2161-2210
[7]   DIELS-ALDER REACTIONS OF HETEROCYCLIC AZADIENES - SCOPE AND APPLICATIONS [J].
BOGER, DL .
CHEMICAL REVIEWS, 1986, 86 (05) :781-793
[8]   When the Pauson-Khand and Pauson-Khand type reactions go awry:: a plethora of unexpected results [J].
Boñaga, LVR ;
Krafft, ME .
TETRAHEDRON, 2004, 60 (44) :9795-9833
[10]   Ruthenium carbonyl-catalyzed [2+2+1]-cycloaddition of ketones, olefins, and carbon monoxide, leading to functionalized γ-butyrolactones [J].
Chatani, N ;
Tobisu, M ;
Asaumi, T ;
Fukumoto, Y ;
Murai, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (30) :7160-7161