Efficient methodology for selective alkylation of hydrazine derivatives

被引：38

作者：

Bredihhin, Aleksei

Groth, Ulrich M.

Maeeorg, Uno

机构：

[1] Univ Tartu, Inst Organ & Bioorgan Chem, EE-51014 Tartu, Estonia

[2] Univ Konstanz, Dept Chem, D-78464 Constance, Germany

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 06期

关键词：

D O I：

10.1021/ol070026w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Formation and use of a nitrogen dianion for selective hydrazine alkylation is reported. The scope and limitations of a new method were demonstrated. The novel method provides fast and easy access to substituted hydrazines, which are widely used as drugs, pesticides, and precursors for a variety of compounds in organic synthesis.

引用

收藏

页码：1097 / 1099

页数：3

相关论文

共 17 条

[1] Increasing the N-H acidity:: Introduction of highly electronegative groups into the hydrazine molecule [J].

Bredikhin, A ;

Tsubrik, O ;

Sillard, R ;

Mäeorg, U .

SYNLETT, 2005, (12) :1939-1941

[2] New synthesis of 1,1-substituted hydrazines by alkylation of N-acyl- or N-alkyloxycarbonylaminophthalimide using the Mitsunobu protocol [J].

Brosse, N ;

Pinto, MF ;

Jamart-Grégoire, B .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (14) :4370-4374

[3] A new synthetic route to protected α-hydrazinoesters in high optical purity using the Mitsunobu protocol [J].

Brosse, N ;

Pinto, MF ;

Bodiguel, J ;

Jamart-Grégoire, B .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (08) :2869-2873

[4]

Brown B. R., 1994, ORGANIC CHEM ALIPHAT, P588

[5]

GREENE TW, 1999, PROTECTIVE GROUPS OR, P737

[6] Stepwise-synthesis of tetrasubstituted hydrazines [J].

Grehn, L ;

Lonn, H ;

Ragnarsson, U .

CHEMICAL COMMUNICATIONS, 1997, (15) :1381-1382

[7] Synthesis and conformational preferences in solution and crystalline states of an aza-tripeptide [J].

Hemmerlin, C ;

Cung, MT ;

Boussard, G .

TETRAHEDRON LETTERS, 2001, 42 (30) :5009-5012

[8] Crystal structures of the main peptidase from the SARS coronavirus inhibited by a substrate-like aza-peptide epoxide [J].

Lee, TW ;

Cherney, MM ;

Huitema, C ;

Liu, J ;

James, KE ;

Powers, JC ;

Eltis, LD ;

James, MNG .

JOURNAL OF MOLECULAR BIOLOGY, 2005, 353 (05) :1137-1151

[9] Synthesis, application and scope of a new protected hydrazine reagent [J].

Mäeorg, U ;

Ragnarsson, U .

TETRAHEDRON LETTERS, 1998, 39 (07) :681-684

[10] Prototypical reagent for the synthesis of substituted hydrazines [J].

Maeorg, U ;

Grehn, L ;

Ragnarsson, U .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (22) :2626-2627