Dihalooxygenation of Alkynes and Alkynols: Preparation of 2,2-Dihaloketones and gem-Dihalolactols

被引:6
作者
Chaisan, Nattawadee [1 ]
Ruengsangtongkul, Sureeporn [2 ]
Thongsornkleeb, Charnsak [1 ,2 ]
Tummatorn, Jumreang [1 ,2 ]
Ruchirawat, Somsak [1 ,2 ]
机构
[1] Chulabhorn Grad Inst, MHESI, Program Chem Biol, Ctr Excellence Environm Hlth & Toxicol EHT,OPS, 54 Kamphaeng Phet 6, Bangkok 10210, Thailand
[2] Chulabhorn Res Inst, Lab Med Chem, 54 Kamphaeng Phet 6, Bangkok 10210, Thailand
关键词
dihaloketones; dihalolactols; alkynes; alkynols; halogenation; N-HALOSUCCINIMIDES; HALOGENATION; CATALYST; KETONES;
D O I
10.1055/a-1774-7077
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A mild and convenient method for the synthesis of 2,2-dihaloketones and gem-dihalolactols has been developed. For the synthesis of 2,2-dihaloketones, alkynes were employed as substrates to react with halogenating agents, Cl-2 or CIBr, that were generated in situ from aqueous HCl and NCS or NBS, respectively. On the other hand, gem-dihalolactols could be prepared from alkynol substrates by using the same reaction conditions. This method could be applied to a broad range of substrates to give the corresponding products in low to good yields.
引用
收藏
页码:1426 / 1430
页数:5
相关论文
共 30 条
[1]  
[Anonymous], THESE WERE OBSERVABL
[2]  
[Anonymous], RESULTS ARE SUMMARIZ
[3]  
[Anonymous], 22 DICHLORO 3 HYDROX
[4]   Synthesis of isocryptolepine analogues and their structure-activity relationship studies as antiplasmodial and antiproliferative agents [J].
Aroonkit, Pasuk ;
Thongsornkleeb, Charnsak ;
Tummatorn, Jumreang ;
Krajangsri, Suppachai ;
Mungthin, Mathirut ;
Ruchirawat, Somsak .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 94 :56-62
[5]   Iron(III) catalyzed halo-functionalization of alkynes [J].
Catano, Bryant ;
Lee, John ;
Kim, Claudia ;
Farrell, David ;
Petersen, Jeffrey L. ;
Xing, Yalan .
TETRAHEDRON LETTERS, 2015, 56 (27) :4124-4127
[6]   Dibrominative Spirocyclization of 2-Butynolyl Anilides: Synthesis of gem-Dibromospirocyclic Benzo[d][1,3]oxazines and Their Application in the Synthesis of 4H-Furo[3,2-b]indoles [J].
Chaisan, Nattawadee ;
Ruengsangtongkul, Sureeporn ;
Tummatorn, Jumreang ;
Ruchirawat, Somsak ;
Chainok, Kittipong ;
Thongsornkleeb, Charnsak .
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (06) :4671-4698
[7]   Stereoselective Halogenation in Natural Product Synthesis [J].
Chung, Won-jin ;
Vanderwal, Christopher D. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (14) :4396-4434
[8]  
D'Oyley JM., 2014, ANGEW CHEM, V126, P10923
[9]   CoFe2O4-SiO2-SO3H nanocomposite as a magnetically recoverable catalyst for oxidative bromination of alkynes [J].
Dutta, Mintu Maan ;
Rajbongshi, Kamal Krishna ;
Phukan, Prodeep .
SYNTHETIC COMMUNICATIONS, 2017, 47 (24) :2330-2341
[10]   Dihalohydration of Alkynols: A Versatile Approach to Diverse Halogenated Molecules [J].
Gibson, Samantha M. ;
D'Oyley, Jarryl M. ;
Higham, Joe I. ;
Sanders, Kate ;
Laserna, Victor ;
Aliev, Abil E. ;
Sheppard, Tom D. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (29) :4018-4028