Concise microwave-assisted synthesis of 2-aminoimidazole marine sponge alkaloids of the isonaamines series

被引：20

作者：

Ermolat'ev, D. S. ^{[1
]}

Alifanov, V. L. ^{[2
]}

Rybakov, V. B. ^{[2
]}

Babaev, E. V. ^{[2
]}

Van der Eycken, E. V. ^{[1
]}

机构：

[1] Univ Louvain, LOMAC, B-3001 Heverlee, Belgium

[2] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119991, Russia

来源：

SYNTHESIS-STUTTGART | 2008年 / 13卷 / 13期

关键词：

natural products; ring opening; cleavage; imidazo[1,2a]pyrimidin-1-ium salts; 2-aminoimidazoles;

D O I：

10.1055/s-2008-1078444

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short and efficient route to 1,4-substituted 2-aminoimidazole alkaloids starting from the easily accessible 2-alkylaminopyrimidines and a.-bromo aldehydes is reported. The formation of the intermediate imidazo[1,2-a]pyrimidinium salts and subsequent cleavage were facilitated by microwave irradiation. Marine sponge alkaloids preclathridines A, C and isonaamines A, C, D were obtained in high yields using the optimized one-pot two-step procedure.

引用

页码：2083 / 2088

页数：6

共 22 条

[1] 2 IMIDAZOLE ALKALOIDS FROM A SPONGE
AKEE, RK
CARROLL, TR
YOSHIDA, WY
SCHEUER, PJ
STOUT, TJ
CLARDY, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) : 1944 - 1946
[2] Novel and efficient synthesis of 2-aminooxazoles from pyrimidin-2(1H)-one
Alifanov, Vadim L.
Babaev, Eugene V.
[J]. SYNTHESIS-STUTTGART, 2007, (02): : 263 - 270
[3] NOVEL MARINE SPONGE ALKALOIDS .2. STRUCTURES AND TOTAL SYNTHESIS OF 2-AMINOIMIDAZOLES FROM A NOTODORIS NUDIBRANCH
ALVI, KA
CREWS, P
LOUGHHEAD, DG
[J]. JOURNAL OF NATURAL PRODUCTS, 1991, 54 (06): : 1509 - 1515
[4] 2-AMINOIMIDAZOLES AND THEIR ZINC-COMPLEXES FROM INDO-PACIFIC LEUCETTA SPONGES AND NOTODORIS NUDIBRANCHS
ALVI, KA
PETERS, BM
HUNTER, LM
CREWS, P
[J]. TETRAHEDRON, 1993, 49 (02) : 329 - 336
[5] Pyrrolo[2,3-d]pyrimidine thymidylate synthase inhibitors:: Design and synthesis of one-carbon bridge derivatives
Aso, K
Imai, Y
Yukishige, K
Ootsu, K
Akimoto, H
[J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2001, 49 (10) : 1280 - 1287
[6] Synthesis of pyrrolo[2,3-d]pyrimidines via cyclocondensation of β-alkoxy- and β-amino-α-bromoaldehydes
Barnett, CJ
Grubb, LM
[J]. TETRAHEDRON LETTERS, 2000, 41 (50) : 9741 - 9745
[7] SYNTHESIS AND LTB(4) RECEPTOR ANTAGONIST ACTIVITIES OF THE NATURALLY-OCCURRING LTB(4) RECEPTOR ANTAGONIST LEUCETTAMINE-A AND RELATED ANALOGS
BOEHM, JC
GLEASON, JG
PENDRAK, I
SARAU, HM
SCHMIDT, DB
FOLEY, JJ
KINGSBURY, WD
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (22) : 3333 - 3340
[8] SIMPLE PYRIMIDINES .3. THE METHYLATION AND STRUCTURE OF THE AMINOPYRIMIDINES
BROWN, DJ
HOERGER, E
MASON, SF
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1955, : 4035 - 4040
[9] NAAMINES AND NAAMIDINES, NOVEL IMIDAZOLE ALKALOIDS FROM THE CALCAREOUS SPONGE LEUCETTA-CHAGOSENSIS
CARMELY, S
KASHMAN, Y
[J]. TETRAHEDRON LETTERS, 1987, 28 (26) : 3003 - 3006
[10] NEW LEUKOTRIENE-B4 RECEPTOR ANTAGONIST - LEUCETTAMINE-A AND RELATED IMIDAZOLE ALKALOIDS FROM THE MARINE SPONGE LEUCETTA-MICRORAPHIS
CHAN, GW
MONG, S
HEMLING, ME
FREYER, AJ
OFFEN, PH
DEBROSSE, CW
SARAU, HM
WESTLEY, JW
[J]. JOURNAL OF NATURAL PRODUCTS, 1993, 56 (01): : 116 - 121

← 1 2 3 →