Combination of hydrazine polyanion strategy and ring-closing metathesis in the synthesis of heterocycles

被引：11

作者：

Tsupova, Svetlana ^{[1
]}

Lebedev, Oleg ^{[1
]}

Maeeorg, Uno ^{[1
]}

机构：

[1] Univ Tartu, Inst Chem, EE-50411 Tartu, Estonia

来源：

TETRAHEDRON | 2012年 / 68卷 / 04期

关键词：

Hydrazines; Heterocycles; Alkylation; Dianion; Ring-closing metathesis; ASYMMETRIC-SYNTHESIS; METHODOLOGY; ALKYLATION;

D O I：

10.1016/j.tet.2011.11.091

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method for the synthesis of cyclic hydrazine derivatives starting from disubstituted hydrazines is reported. The method is based on the selective alkylation of hydrazine dianions with bromoalkenes and subsequent cyclization using Grubbs' catalysts. The described method provides fast and easy access to the substrates for ring-closing metathesis and the corresponding heterocycles containing a hydrazine moiety. The scope and limitations of the new method are also demonstrated. (C) 2011 Elsevier Ltd. All rights reserved.

引用

收藏

页码：1011 / 1016

页数：6

相关论文

共 22 条

[1] Synthesis, biological evaluation and structural determination of β-aminoacyl-containing cyclic hydrazine derivatives as dipeptidlyl peptidase IV (DPP-IV) inhibitors [J].

Ahn, Jin Hee ;

Shin, Mi Sik ;

Jun, Mi Ae ;

Jung, Sun Ho ;

Kang, Seung Kyu ;

Kim, Kwang Rok ;

Dal Rhee, Sang ;

Kang, Nam Sook ;

Kim, Sun Young ;

Sohn, Sang-Kwon ;

Kim, Sung Gyu ;

Jin, Mi Sun ;

Lee, Jie Oh ;

Cheon, Hyae Gyeong ;

Kim, Sung Soo .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (09) :2622-2628

[2] Lipase TL-mediated kinetic resolution of 5-benzyloxy-1-tert-butyldimethylsilyloxy-2-pentanol at low temperature:: Concise asymmetric synthesis of both enantiomers of a piperazic acid derivative [J].

Aoyagi, Y ;

Saitoh, Y ;

Ueno, T ;

Horiguchi, M ;

Takeya, K ;

Williams, RM .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18) :6899-6904

[3] Structure of N,N′-Bis(amino acids) in the Solid State and in Solution. A 13C and 15N CPMAS NMR Study [J].

Ballano, Genia ;

Jimenez, Ana I. ;

Cativiela, Carlos ;

Claramunt, Rosa M. ;

Sanz, Dionisia ;

Alkorta, Ibon ;

Elguero, Jose .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (21) :8575-8578

[4] Effective strategy for the systematic synthesis of hydrazine derivatives [J].

Bredihhin, Aleksei ;

Maeorg, Uno .

TETRAHEDRON, 2008, 64 (28) :6788-6793

[5] Use of polyanions for alkylation of hydrazine derivatives [J].

Bredihhin, Aleksei ;

Maeorg, Uno .

ORGANIC LETTERS, 2007, 9 (24) :4975-4977

[6] Efficient methodology for selective alkylation of hydrazine derivatives [J].

Bredihhin, Aleksei ;

Groth, Ulrich M. ;

Maeeorg, Uno .

ORGANIC LETTERS, 2007, 9 (06) :1097-1099

[7]

Jensen H. H., 2002, J CHEM SOC P1, V33, P1190

[8] The use of polyanions of hydrazines in the synthesis of heterocycles [J].

Lebedev, Oleg ;

Bredihhin, Aleksei ;

Tsupova, Svetlana ;

Maeorg, Uno .

TETRAHEDRON, 2009, 65 (27) :5438-5442

[9] Organocatalytic α-amination-allylation-RCM strategy:: enantioselective synthesis of cyclic hydrazines [J].

Lim, Aram ;

Choi, Jung Hoon ;

Tae, Jinsung .

TETRAHEDRON LETTERS, 2008, 49 (33) :4882-4885

[10] Synthesis of N-propargylphenelzine and analogues as neuroprotective agents [J].

Ling, L ;

Urichuk, LJ ;

Sloley, BD ;

Coutts, RT ;

Baker, GB ;

Shan, JJ ;

Pang, PKT .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (20) :2715-2717