A convenient solution and solid-phase synthesis of Δ5-2-oxopiperazines via N-acyliminium ions cyclization

被引:87
作者
Cheng, JF [1 ]
Chen, M [1 ]
Arrhenius, T [1 ]
Nadzan, A [1 ]
机构
[1] LLC, Chugai Pharma USA, Dept Chem, San Diego, CA 92121 USA
关键词
D O I
10.1016/S0040-4039(02)01403-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An extremely efficient synthesis of Delta(5)-2-oxopiperazines in solution phase and on solid support has been established via a Ugi four-component condensation reaction (U-4CC) followed by N-acyliminium ion cyclization between the aldehyde (acetal) functionality and the newly formed amide bond. The desired Delta(5)-2-oxopiperazines are obtained in excellent yields and purity. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6293 / 6295
页数:3
相关论文
共 16 条
[1]   SOLID-PHASE PEPTIDE-SYNTHESIS BY 4 COMPONENT CONDENSATION - PEPTIDE FORMATION ON AN ISOCYANO POLYMER SUPPORT [J].
ARSHADY, R ;
UGI, I .
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1981, 36 (09) :1202-1203
[2]   Derivatized oxopiperazine rings from amino acids [J].
Bhatt, U ;
Mohamed, N ;
Just, G ;
Roberts, E .
TETRAHEDRON LETTERS, 1997, 38 (21) :3679-3682
[3]   Solid-phase synthesis and structural analysis of bicyclic β-turn mimetics incorporating functionality at the i to i+3 positions [J].
Eguchi, M ;
Lee, MS ;
Nakanishi, H ;
Stasiak, M ;
Lovell, S ;
Kahn, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (51) :12204-12205
[4]   The solution phase synthesis of diketopiperazine libraries via the Ugi reaction: Novel application of Armstrong's convertible isonitrile. [J].
Hulme, C ;
Morrissette, MM ;
Volz, FA ;
Burns, CJ .
TETRAHEDRON LETTERS, 1998, 39 (10) :1113-1116
[5]   A remarkable two-step synthesis of diverse 1,4-benzodiazepine-2,5-diones using the Ugi four-component condensation [J].
Keating, TA ;
Armstrong, RW .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (25) :8935-8939
[6]  
KONH W, 2001, TETRAHEDRON LETT, V42, P4453
[7]   The current status of heterocyclic combinatorial libraries [J].
Nefzi, A ;
Ostresh, JM ;
Houghten, RA .
CHEMICAL REVIEWS, 1997, 97 (02) :449-472
[8]   Efficient synthesis of conformationally constrained peptidomimetics containing 2-oxopiperazines [J].
Pohlmann, A ;
Schanen, V ;
Guillaume, D ;
Quirion, JC ;
Husson, HP .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (04) :1016-1022
[9]   An efficient and versatile synthesis of piperazine-2-carboxamides [J].
Rossen, K ;
Sager, J ;
DiMichele, LM .
TETRAHEDRON LETTERS, 1997, 38 (18) :3183-3186
[10]   Exploitation of the Ugi 4CC reaction: Preparation of small molecule combinatorial libraries via solid phase [J].
Short, KM ;
Ching, BW ;
Mjalli, AMM .
TETRAHEDRON, 1997, 53 (19) :6653-6679