A Direct Cycloaminative Approach to Imidazole Derivatives via Dual C-H Functionalization

被引：31
作者：
Arepally, Sagar [1 ]
Babu, Venkata Nagarjuna [1 ]
Bakthadoss, Manickam [2 ]
Sharada, Duddu S. [1 ]
机构：
[1] Indian Inst Technol Hyderabad, Dept Chem, Sangareddy 502285, Telangana, India
[2] Pondicherry Univ, Dept Chem, Pondicherry 605014, India
来源：
ORGANIC LETTERS | 2017年 / 19卷 / 19期
关键词：
N BOND FORMATION; CARBON-NITROGEN BONDS; AMINATION REACTIONS; NATURAL-PRODUCTS; HETEROCYCLIC CARBENES; COUPLING REACTIONS; POLYVALENT IODINE; FORMING REACTIONS; ORGANIC AZIDES; ARYL HALIDES;
D O I：
10.1021/acs.orglett.7b01840
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Organoiodine(III)-promoted C(sp(3))-H azidation was a key step for the cycloaminative process. An unprecedented method for metal-free dehydrogenative N-incorporation into C(sp(3))-H and C(sp(2))-H bonds for the synthesis of diverse imidazoles has been disclosed. The overall transformation involves the construction of four C-N bonds through hydroamination-azidation-cyclization sequence. The reaction can be easily handled and proceeds under mild conditions. Further, the potential of the present strategy is revealed by the practical synthesis of N-heterocyclic carbene (NHC) precursors.
引用
收藏
页码：5014 / 5017
页数：4
相关论文
共 68 条
[11]  
De Luca L, 2006, CURR MED CHEM, V13, P1
[12]   Transition metal-catalyzed synthesis of pyrroles from dienyl azides [J].
Dong, Huijun ;
Shen, Meihua ;
Redford, Joanne E. ;
Stokes, Benjamin J. ;
Pumphrey, Ashley L. ;
Driver, Tom G. .
ORGANIC LETTERS, 2007, 9 (25) :5191-5194
[13]   Recent developments in the chemistry of enaminones [J].
Elassar, AZA ;
El-Khair, AA .
TETRAHEDRON, 2003, 59 (43) :8463-8480
[14]   Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis [J].
Evano, Gwilherm ;
Blanchard, Nicolas ;
Toumi, Mathieu .
CHEMICAL REVIEWS, 2008, 108 (08) :3054-3131
[15]   Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes [J].
Flanigan, Darrin M. ;
Romanov-Michailidis, Fedor ;
White, Nicholas A. ;
Rovis, Tomislav .
CHEMICAL REVIEWS, 2015, 115 (17) :9307-9387
[16]  
Greenhill J.V., 1996, Adv. Heterocycl. Chem, V67, P207, DOI [10.1016/S0065-2725(08)60072-0, DOI 10.1016/S0065-2725(08)60072-0]
[17]  
GREENHILL JV, 1977, CHEM SOC REV, V6, P277, DOI 10.1039/cs9770600277
[18]   PALLADIUM-CATALYZED AROMATIC AMINATIONS WITH IN-SITU GENERATED AMINOSTANNANES [J].
GURAM, AS ;
BUCHWALD, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (17) :7901-7902
[19]   A new synthesis of carmethizole and related nitrogen analogues [J].
Hay, MP ;
Denny, WA .
TETRAHEDRON LETTERS, 1997, 38 (48) :8425-8428
[20]   Design, synthesis and evaluation of imidazolylmethyl carbamate prodrugs of alkylating agents [J].
Hay, MP ;
Wilson, WR ;
Denny, WA .
TETRAHEDRON, 2000, 56 (04) :645-657
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