Synthesis and reactions of 2-substituted ethyl N-alkylmalonylhydroxamic acids

被引：24

作者：

Hoffman, RV ^{[1
]}

Madan, S ^{[1
]}

机构：

[1] New Mexico State Univ, Dept Chem & Biochem, Las Cruces, NM 88003 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 12期

关键词：

D O I：

10.1021/jo0300690

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Alkylation of O-silylated N-alkylmalonylhydroxamic acids provides a method for the synthesis of 2-substituted N-alkylmalonyl hydroxamic acids. The substituent at C-2 does not materially change the chemistry of the a-lactam intermediates produced from them. They can be converted to unsymmetric ureas and hydantoins in high yields. The addition of unsaturated substituents at C-2 is used to produce cyclic ureas containing medium rings via RCM reactions.

引用

页码：4876 / 4885

页数：10

共 16 条

[1] USEFUL HYDROXYLAMINE DERIVATIVES FOR THE SYNTHESIS OF HYDROXAMIC ACIDS [J].

ALTENBURGER, JM ;

MIOSKOWSKI, C ;

DORCHYMONT, H ;

SCHIRLIN, D ;

SCHALK, C ;

TARNUS, C .

TETRAHEDRON LETTERS, 1992, 33 (35) :5055-5058

[2] Ring closure metathesis of indole 2-carboxylic acid allylamide derivatives [J].

Chacun-Lefèvre, L ;

Bénéteau, V ;

Joseph, B ;

Mérour, JY .

TETRAHEDRON, 2002, 58 (51) :10181-10188

[3] PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES [J].

COREY, EJ ;

VENKATESWARLU, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) :6190-+

[4] A NEW MODE OF REACTIVITY OF N-METHOXY-N-METHYLAMIDES WITH STRONGLY BASIC REAGENTS [J].

GRAHAM, SL ;

SCHOLZ, TH .

TETRAHEDRON LETTERS, 1990, 31 (44) :6269-6272

[5] ORIGINS OF REGIOSELECTIVITY IN THE REACTIONS OF ALPHA-LACTAMS WITH NUCLEOPHILES [J].

HOFFMAN, RV ;

NAYYAR, NK ;

CHEN, WT .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (13) :4121-4125

[6] The reactions of hydrazines with α-lactams.: Regiochemistry of hydrazine addition and subsequent ring closure to N-aminohydantoins or 1,2,4-triazine-3,6-diones [J].

Hoffman, RV ;

Reddy, MM ;

Klumas, CM ;

Cervantes-Lee, F .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (24) :9128-9130

[7] REACTION OF HYDRAZINES WITH ALPHA-LACTAMS FOR THE PREPARATION OF 1,2,4-TRIAZINE-3,6-DIONES AND AZA-UREA PEPTIDE MIMETICS [J].

HOFFMAN, RV ;

NAYYAR, NK .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18) :5992-5994

[8] Improved methodology for the generation and trapping of α-lactams by weak nucleophiles [J].

Hoffman, RV ;

Reddy, MM ;

Cervantes-Lee, F .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (08) :2591-2595

[9] A FACILE PREPARATION OF N-(ISOPROPOXYALKYL) AMIDES BY GENERATION AND TRAPPING OF N-ACYLIMINIUM IONS FROM IONIZATION-REARRANGEMENT REACTIONS OF N-TRIFLYLOXY AMIDES [J].

HOFFMAN, RV ;

NAYYAR, NK .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (13) :3530-3539

[10] ALPHA-LACTAM INTERMEDIATES IN BASE-PROMOTED REACTIONS OF O-SULFONYLATED HYDROXAMIC ACIDS WITH NUCLEOPHILES [J].

HOFFMAN, RV ;

NAYYAR, NK ;

CHEN, WT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (12) :5031-5034

← 1 2 →