SYNTHESIS OF 2-DIMETHYLAMINOIMIDAZOLE DERIVATIVES - A NEW ACCESS TO INDOLYL-IMIDAZOLE ALKALOIDS OF MARINE ORIGIN

被引：29

作者：

DALKAFOUKI, A ^{[1
]}

ARDISSON, J ^{[1
]}

KUNESCH, N ^{[1
]}

LACOMBE, L ^{[1
]}

POISSON, JE ^{[1
]}

机构：

[1] COLL FRANCE,CNRS,CHIM INTERACT MOLEC LAB,F-75231 PARIS 05,FRANCE

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 39期

关键词：

INDOLYL-IMIDAZOLES; ALKALOIDS; APLYSINOPSIN; 2-DIMETHYLAMINOIMIDAZOLE; MARINE PRODUCTS;

D O I：

10.1016/S0040-4039(00)92376-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first preparation of 2-dimethylaminoimidazole 1a, a structural feature of several marine products was undertaken and its reactivity investigated. The synthesis of natural alkaloids 5 and 12b was achieved by direct coupling of the easily accessible oxidized 2-dimethylaminoimidazoles 7 and 8 with indole-3-carboxaldehyde and indole respectively, demonstrating the usefulness of this approach for other structurally related natural products.

引用

页码：5325 / 5328

页数：4

共 50 条

[31] One-Pot Regioselective Synthesis of Imidazole and 2,3-Dihydroquinazolinone Derivatives - An Easy Access to 'Nature-Like Molecules'; Part XIII in the Series: 'Studies on Novel Synthetic Methodologies'
Sashidhara, Koneni V.
Palnati, Gopala Reddy
Dodda, Ranga Prasad
Avula, Srinivasa Rao
Swami, Priyanka
SYNLETT, 2013, 24 (14) : 1795 - 1800
[32] SYNTHESIS, ANTIBACTERIAL ACTIVITY STUDY OF NEW 3-((5-METHOXY-1H- BENZO[d]IMIDAZOLE-2-YLTHIO)METHYL)-2-CHLOROQUINOLINE DERIVATIVES
Pokalwar, Rajkumar U.
Survase, Avinash A.
Kadam, Avdhut D.
HETEROCYCLIC LETTERS, 2022, 12 (03): : 587 - 596
[33] Synthesis of New C- and N-β-D-Glucopyranosyl Derivatives of Imidazole, 1,2,3-Triazole and Tetrazole, and Their Evaluation as Inhibitors of Glycogen Phosphorylase
Kun, Sandor
Bokor, Eva
Sipos, Adam
Docsa, Tibor
Somsak, Laszlo
MOLECULES, 2018, 23 (03):
[34] Stereoselective synthesis of 3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one derivatives as PIM kinase inhibitors inspired from marine alkaloids
Casuscelli, Francesco
Ardini, Elena
Avanzi, Nilla
Badari, Alessandra
Casale, Elena
Disingrini, Teresa
Donati, Daniele
Ermoli, Antonella
Felder, Eduard R.
Galvani, Arturo
Isacchi, Antonella
Menichincheri, Maria
Montemartini, Marisa
Orrenius, Christian
Piutti, Claudia
Salom, Barbara
Papeo, Gianluca
CHIRALITY, 2022, 34 (11) : 1437 - 1452
[35] Synthesis and antimicrobial activity of some new of 2-(furan-2-yl)-1-(piperidin-4-yl)-1H-benzo[d]imidazole derivatives
Parmar, Tejasvi H.
Sangani, Chetan B.
Parmar, Nilesh D.
Bhalodiya, Pradip C.
ARKIVOC, 2018, : 471 - 481
[36] SYNTHESIS OF NEW IMIDAZOLE DERIVATIVES FROM 1-(1-METHYL IMIDAZOL-2-YL METHYL)-2,4,6 TRIPHENYLPYRIDINIUM TETRAFLUOROBORATE WITH ANIONS OF SECONDARY NITROALKANES
VANELLE, P
JENTZER, O
CROZET, MP
MALDONADO, J
COMPTES RENDUS DE L ACADEMIE DES SCIENCES SERIE II, 1989, 308 (15): : 1341 - 1344
[37] PARTIAL SYNTHESIS OF NEW ERGOLINE DERIVATIVES FROM CLAVINE ALKALOIDS, .4. AGROCLAVINES MONOSUBSTITUTED AT N-1, C-2, AND N-6
EICH, E
SIEBEN, R
BECKER, C
ARCHIV DER PHARMAZIE, 1985, 318 (03) : 214 - 218
[38] Cyclopropyl building blocks in organic synthesis, 51 - An easy access to 1-azaspiropentane-2-carboxamides - The first derivatives of a new type of amino acids
Tamm, M
Thutewohl, M
Ricker, CB
Bes, MT
de Meijere, A
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1999, 1999 (09) : 2017 - 2024
[39] ASYMMETRIC-SYNTHESIS .32. A NEW ACCESS TO ENANTIOMERICALLY PURE (S)-(-)-PIPECOLIC ACID AND 2-ALKYLATED OR 6-ALKYLATED DERIVATIVES
BERRIEN, JF
ROYER, J
HUSSON, HP
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (14): : 3769 - 3774
[40] NEW DERIVATIVES OF ETHYL 1-METHYL-1H-IMIDAZOLE-2-GLYOXYLATE - SYNTHESIS AND PROPERTIES OF ALPHA-HYDROXYIMINO AND ALPHA-METHOXYIMINO DOUBLE-BOND STEREOISOMERS
ELITROPI, G
TRICERRI, S
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1979, 16 (07) : 1385 - 1387

← 1 2 3 4 5 →