Efficient synthesis of new butenolides by subsequent reactions: application for the synthesis of original iminolactones, bis-iminolactones and bis-lactones

被引：30

作者：

Cheikh, Nawel ^{[1
,2
,3
,4
]}

Bar, Nathalie ^{[1
,2
]}

Choukchou-Braham, Nourredine ^{[3
]}

Mostefa-Kara, Bachir ^{[3
]}

Lohier, Jean-Francois ^{[1
,2
]}

Sopkova, Jana ^{[5
]}

Villemin, Didier ^{[1
,2
]}

机构：

[1] ENSICAEN, Lab Chim Mol & Thioorgan, CNRS, UMR 6507,INC3M,FR 3038, F-14050 Caen, France

[2] Univ Caen Basse Normandie, F-14050 Caen, France

[3] Univ Abou Bakr Belkaid, Fac Sci, Lab Catalyse & Synth Chim Organ, Tilimsen 13000, Algeria

[4] Univ Bechar, Fac Sci & Technol, Bechar 08000, Algeria

[5] Univ Caen, CERMN, F-14032 Caen, France

来源：

TETRAHEDRON | 2011年 / 67卷 / 08期

关键词：

N-Substituted cyanoacetamide; Iminolactone; Butenolide; Diamine; Bis-iminolactone; Bis-lactone; ANNONACEOUS ACETOGENINS; STEREOSELECTIVE-SYNTHESIS; SUBSTITUTED BUTENOLIDES; PART I; MICROWAVE; METHODOLOGY; INHIBITOR; CHEMISTRY; MECHANISM; EXCHANGE;

D O I：

10.1016/j.tet.2010.12.062

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed the synthesis of twenty four new iminolactones, bis-iminolactones and bis-lactones by subsequent esterification-condensation or addition-condensation reactions according to two strategies from alpha-hydroxyketones. The X-ray diffraction data of a bis-iminolactone is described and present an interesting helical column packing. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：1540 / 1551

页数：12

共 54 条

[1] Synthesis of new bis-iminocoumarins by Schmidt reaction catalyzed by ion-exchange resins
Ammar, H
Fakhfakh, M
Le Bigot, Y
El Gharbi, R
[J]. SYNTHETIC COMMUNICATIONS, 2003, 33 (11) : 1821 - 1828
[2] [Anonymous], 1999, THESIS U CAEN
[3] Avetisyan A.A., 1977, RUSSCHEMREV, V46, P643, DOI [10.1070/RC1977v046n07ABEH002162, DOI 10.1070/RC1977V046N07ABEH002162]
[4] AVETISYAN AA, 1977, ARM KHIM ZH, V30, P90
[5] The formation and stabillity of spiro-compounds. Part I. Spiro-compounds from cyclo-hexane.
Beesley, RM
Ingold, CK
Thorpe, JF
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1915, 107 : 1080 - 1106
[6] BERNAY E, 2012, BER, V45, P3682
[7] ADDITION OF L-CYSTEINE TO UNSATURATED LACTONES AND RELATED COMPOUNDS
BLACK, DK
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1966, (12): : 1123 - &
[8] Parallel liquid-phase synthesis of benzopyrano[2,3-d]pyrimidine libraries
Borisov, Alexander V.
Dzhavakhishvili, Sergey G.
Zhuravel, Irina O.
Kovalenko, Sergiy M.
Nikitchenko, Victor M.
[J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2007, 9 (01): : 5 - 8
[9] Short and efficient synthesis of cadiolide B
Boukouvalas, J
Pouliot, M
[J]. SYNLETT, 2005, (02) : 343 - 345
[10] General, regiodefined access to α-substituted butenolides through metal-halogen exchange of 3-bromo-2-silyloxyfurans.: Efficient synthesis of an anti-inflammatory gorgonian lipid
Boukouvalas, John
Loach, Richard P.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (20) : 8109 - 8112

← 1 2 3 4 5 6 →