Synthesis of functionalized nitrogen heterocycles from β- and γ-amino acids by radical decarboxylation

被引:17
作者
Boto, A
Hernández, R
de León, Y
Murguía, JR
Rodríguez-Afonso, A
机构
[1] CSIC, Inst Prod Nat & Agrobiol, San Cristobal la Laguna 38206, Tenerife, Spain
[2] Hosp Univ Canarias, Unidad Invest, San Cristobal la Laguna 38320, Tenerife, Spain
关键词
radicals; piperidines; arylpiperidines; pyrrolidines; decarboxylation; amino acids; antifungic;
D O I
10.1016/j.tetlet.2004.07.111
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The radical decarboxylation of beta- and gamma-amino acids on treatment with Phl(OAC)(2)-I-2 is a mild and efficient methodology to synthesize halogenated or oxygenated nitrogen heterocycles. The reaction was applied to the synthesis of bioactive products, such as opioid analogues, iminosugars and new antifungic agents. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6841 / 6845
页数:5
相关论文
共 72 条
[1]  
Alcaide B, 2002, EUR J ORG CHEM, V2002, P1595
[2]   Sugar-mimic glycosidase inhibitors: natural occurrence, biological activity and prospects for therapeutic application [J].
Asano, N ;
Nash, RJ ;
Molyneux, RJ ;
Fleet, GWJ .
TETRAHEDRON-ASYMMETRY, 2000, 11 (08) :1645-1680
[3]   CHEMICALS FROM THE GLANDS OF ANTS [J].
ATTYGALLE, AB ;
MORGAN, ED .
CHEMICAL SOCIETY REVIEWS, 1984, 13 (03) :245-278
[4]   Asymmetric routes to substituted piperidines [J].
Bailey, PD ;
Millwood, PA ;
Smith, PD .
CHEMICAL COMMUNICATIONS, 1998, (06) :633-640
[5]   Synthesis of heterocycles via group VI Fischer carbene complexes [J].
Barluenga, J ;
Santamaría, J ;
Tomás, M .
CHEMICAL REVIEWS, 2004, 104 (05) :2259-2283
[6]  
Beck G, 2002, SYNLETT, P837
[7]   1-aza sugars, apparent transition state analogues of equatorial glycoside formation/cleavage [J].
Bols, M .
ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (01) :1-8
[8]   Synthesis of 2,3-disubstituted pyrrolidines and piperidines via one-pot oxidative decarboxylation-β-iodination of amino acids [J].
Boto, A ;
Hernández, R ;
de León, Y ;
Suárez, E .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (23) :7796-7803
[9]   Tandem oxidative radical decarboxylation-β-iodination of amino acids.: Application to the synthesis of chiral 2,3-disubstituted pyrrolidines [J].
Boto, A ;
Hernández, R ;
Suárez, E .
TETRAHEDRON LETTERS, 2000, 41 (14) :2495-2498
[10]   Tandem radical decarboxylation-oxidation of amino acids:: A mild and efficient method for the generation of N-acyliminium ions and their nucleophilic trapping [J].
Boto, A ;
Hernández, R ;
Suárez, E .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (16) :4930-4937