Reaction of 2-bromomethylazoles and TosMIC: A domino process to azolopyrimidines. Synthesis of core tricycle of the variolins alkaloids

被引：43

作者：

Mendiola, J ^{[1
]}

Minguez, JM ^{[1
]}

Alvarez-Builla, J ^{[1
]}

Vaquero, JJ ^{[1
]}

机构：

[1] Univ Alcala de Henares, Dept Quim Organ, E-28871 Alcala De Henares, Spain

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 21期

关键词：

D O I：

10.1021/ol0062087

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

GRAPHICS A new reaction of N protected 2-bromomethylazoles and tosylmethyl isocyanide (TosMIC) leading to the preparation of azolopyrimidines is described. This domino sequence was used to synthesize the pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine core of alkaloids variolins from 4-methoxy-2-methylpyrrolo[2,3-b]pyrimidine in two steps.

引用

页码：3253 / 3256

页数：4

共 13 条

[1] Alvarez M, 1999, SYNTHESIS-STUTTGART, P615
[2] ALVAREZ M, 1999, J CHEM SOC P1, P215
[3] CHEMISTRY OF INDOLO[1,2-C]QUINAZOLINE - AN APPROACH TO THE MARINE ALKALOID HINCKDENTINE-A
BILLIMORIA, AD
CAVA, MP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (22) : 6777 - 6782
[4] HINCKDENTINE-A - A NOVEL ALKALOID FROM THE MARINE BRYOZOAN HINCKSINOFLUSTRA-DENTICULATA
BLACKMAN, AJ
HAMBLEY, TW
PICKER, K
TAYLOR, WC
THIRASASANA, N
[J]. TETRAHEDRON LETTERS, 1987, 28 (45) : 5561 - 5562
[5] HETEROCYCLIZATIONS .8. NEW POLYCYCLIC PYRIMIDINES WITH BRIDGE-HEAD NITROGEN
CAPUANO, L
SCHREPFER, HJ
MULLER, K
ROOS, H
[J]. CHEMISCHE BERICHTE-RECUEIL, 1974, 107 (03): : 929 - 936
[6] THE SYNTHESIS OF 5-AZAINDOLES BY SUBSTITUTION-REARRANGEMENT OF 7-AZAINDOLES UPON TREATMENT WITH CERTAIN PRIMARY AMINES
GIRGIS, NS
LARSON, SB
ROBINS, RK
COTTAM, HB
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1989, 26 (02) : 317 - 325
[7] Silver acetate catalysed cycloadditions of isocyanoacetates
Grigg, R
Lansdell, MI
Thornton-Pett, M
[J]. TETRAHEDRON, 1999, 55 (07) : 2025 - 2044
[8] Pyrrolodiazines.: 5.: Synthesis, structure, and chemistry of pyrrolo[1,2-c]pyrimidine.: Dipolar cycloaddition of pyrrolo[1,2-c]pyrimidinium ylides
Minguez, JM
Vaquero, JJ
Alvarez-Builla, J
Castaño, O
Andrés, JL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (21) : 7788 - 7801
[9] Improved synthesis of pyrrolo[1,2-c]pyrimidine and derivatives
Minguez, JM
Vaquero, JJ
GarciaNavio, JL
AlvarezBuilla, J
[J]. TETRAHEDRON LETTERS, 1996, 37 (24) : 4263 - 4266
[10] ALKALOIDS FROM THE ANTARCTIC SPONGE KIRKPATRICKIA-VARIALOSA .1. VARIOLIN-B, A NEW ANTITUMOR AND ANTIVIRAL COMPOUND
PERRY, NB
ETTOUATI, L
LITAUDON, M
BLUNT, JW
MUNRO, MHG
PARKIN, S
HOPE, H
[J]. TETRAHEDRON, 1994, 50 (13) : 3987 - 3992

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