Fused Bis-lactams to Spirolactams: A New Member of the Family of Ring-Contraction Reaction

被引：1

作者：

Chaubet, Guilhem ^{[1
]}

Berthet, Matheo ^{[1
]}

Pasco, Morgane ^{[1
]}

Cazals, Guillaume ^{[1
]}

Lebrun, Aurelien ^{[1
]}

Martinez, Jean ^{[1
]}

Parrot, Isabelle ^{[1
]}

机构：

[1] Univ Montpellier, ENSCM, IBMM, CNRS,UMR 5247, CC 17-03,Pl E Bataillon, F-34095 Montpellier 5, France

来源：

LETTERS IN ORGANIC CHEMISTRY | 2018年 / 15卷 / 12期

关键词：

Spirolactams; ring-contraction; heterocycles; homologous; cyclic compound; pyrrole; TRANSANNULAR REARRANGEMENT; STEREOSELECTIVE-SYNTHESIS; DIKETOPIPERAZINES;

D O I：

10.2174/1570178615666180326160131

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new ring contraction of fused bis-lactams into spirolactams is presented here. In the presence of a triflate catalyst in various solvents under microwave irradiation, this rearrangement allows a clean conversion of some fused bicycles into spirocycles with good yields. The interest of this work thus lies in the use of activated 2,5-diketopiperazines as starting materials and demonstrates the wide range of applications of ring contraction reactions.

引用

收藏

页码：1046 / 1055

页数：10

相关论文

共 15 条

[1] New building blocks for iminosugars: a concise synthesis of polyhydroxylated N-alkoxypiperidines through an intramolecular azepine ring contraction [J].

Barnes, Korry L. ;

Chen, Kelly ;

Catalano, Vincent J. ;

Jeffrey, Christopher S. .

Organic Chemistry Frontiers, 2015, 2 (05) :497-501

[2]

Butkus E., 2014, Comprehensive Organic Synthesis, VSecond, P853

[3] From Diketopiperazines to Hydantoins: An Unprecedented Rearrangement [J].

Chaubet, Guilhem ;

Cazals, Guillaume ;

Lebrun, Aurelien ;

Martinez, Jean ;

Parrot, Isabelle .

SYNLETT, 2014, 25 (04) :574-578

[4] Stereoselective synthesis of original spirolactams displaying promising folded structures [J].

Chaubet, Guilhem ;

Coursindel, Thibault ;

Morelli, Xavier ;

Betzi, Stephane ;

Roche, Philippe ;

Guari, Yannick ;

Lebrun, Aurelien ;

Toupet, Loic ;

Collette, Yves ;

Parrot, Isabelle ;

Martinez, Jean .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (28) :4719-4726

[5] Total Synthesis of (±)-Gelsemoxonine [J].

Diethelm, Stefan ;

Carreira, Erick M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (23) :8500-8503

[6] Transannular rearrangement of activated lactams: Stereoselective synthesis of substituted pyrrolidine-2,4-diones from diketopiperazines [J].

Farran, Daniel ;

Parrot, Isabelle ;

Martinez, Jean ;

Dewynter, Georges .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (39) :7488-7490

[7] Transannular rearrangement of activated 2,5-diketopiperazines: a key route to original scaffolds [J].

Farran, Daniel ;

Parrot, Isabelle ;

Toupet, Loic ;

Martinez, Jean ;

Dewynter, Georges .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (21) :3989-3996

[8]

Hart H, 1971, ADV ALICYCLIC CHEM, V3

[9] Oxetanes from the Ring Contraction of α-Triflates of γ-Lactones: Oxetane Nucleosides and Oxetane Amino Acids [J].

Jenkinson, Sarah F. ;

Fleet, George W. J. .

CHIMIA, 2011, 65 (1-2) :71-75

[10] Ring contraction methodology for the synthesis of pyrroles [J].

Joshi, U ;

Pipelier, M ;

Naud, S ;

Dubreuil, D .

CURRENT ORGANIC CHEMISTRY, 2005, 9 (03) :261-288