Synthesis of Triazafluoranthenones via Silver(I)-Mediated Nonoxidative and Oxidative Intramolecular Palladium-Catalyzed Cyclizations

被引：27

作者：

Koutentis, Panayiotis A. ^{[1
]}

Loizou, Georgia ^{[1
]}

Lo Re, Daniele ^{[1
]}

机构：

[1] Univ Cyprus, Dept Chem, CY-1678 Nicosia, Cyprus

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 14期

关键词：

1ST TOTAL-SYNTHESIS; ANILIDE ORTHO-ARYLATION; C-H FUNCTIONALIZATION; ENDOPHENAZINES A-D; CARBAZOLE ALKALOIDS; ORGANIC-SYNTHESIS; AZAFLUORANTHENE ALKALOIDS; PHENAZINE ANTIBIOTICS; BIOLOGICAL EVALUATION; PROMOTED SYNTHESIS;

D O I：

10.1021/jo200966k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Silver(I) fluoride (AgF)-mediated intramolecular nonoxidative and oxidative palladium-catalyzed cyclizations of 1,3-diphenyl- and 8-iodo-1,3-diphenylbenzo[e][1,2,4]triazin-7(1H)-ones 6a (R = H) and 7a (R = I) afford a new 'alkaloid like' ring system 2-phenyl-6H-[1,2,4]triazino[5,6,1-jk]carbazol-6-one 8a (triazafluoranthenone) in 86 and 100% yields, respectively. Furthermore, these cyclization protocols were used to prepare triazafluoranthenone analogues 8b-e bearing dialkylamino, methoxy, and phenylsulfanyl substituents at C-5, which were also independently synthesized from triazafluoranthenone 8a by regioselective nucleophilic addition. Similar AgF-mediated intramolecular nonoxidative and oxidative palladium-catalyzed.cyclizations of 8,10-dihydro-1-iodo-10-phenylphenazin-2(7H)-ones 13 gave the new 'alkaloid like' ring system 8H-indolo[1,2,3-mn]phenazin-8-one 14 in 80 and 18% yields, respectively.

引用

页码：5793 / 5802

页数：10

共 78 条

[1] CATALYTIC OXIDATIVE AROMATIC CYCLIZATIONS WITH PALLADIUM
AKERMARK, B
OSLOB, JD
HEUSCHERT, U
[J]. TETRAHEDRON LETTERS, 1995, 36 (08) : 1325 - 1326
[2] AKERMARK B, 1975, J ORG CHEM, V40, P1365, DOI 10.1021/jo00897a048
[3] PALLADIUM-CATALYZED CYCLIZATION OF 2-SUBSTITUTED HALOGENOARENES BY DEHYDROHALOGENATION
AMES, DE
OPALKO, A
[J]. TETRAHEDRON, 1984, 40 (10) : 1919 - 1925
[4] ANTITUBERCULOSIS ACTIVITY IN THE PHENAZINE SERIES - ISOMERIC PIGMENTS OBTAINED BY OXIDATION OF O-PHENYLENEDIAMINE DERIVATIVES
BARRY, VC
CONALTY, ML
GAFFNEY, EE
[J]. JOURNAL OF PHARMACY AND PHARMACOLOGY, 1956, 8 (12) : 1089 - 1096
[5] Antitumor agents.: 2.: Synthesis, structure-activity relationships, and biological evaluation of substituted 5H-pyridophenoxazin-5-ones with potent antiproliferative activity
Bolognese, A
Correale, G
Manfra, M
Lavecchia, A
Mazzoni, O
Novellino, E
Barone, V
La Colla, P
Loddo, R
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (24) : 5217 - 5223
[6] Antitumor agents.: 1.: Synthesis, biological evaluation, and molecular modeling of 5H-pyrido[3,2-a]phenoxazin-5-one, a compound with potent antiproliferative activity
Bolognese, A
Correale, G
Manfra, M
Lavecchia, A
Mazzoni, O
Novellino, E
Barone, V
Pani, A
Tramontano, E
La Colla, P
Murgioni, C
Serra, I
Setzu, G
Loddo, R
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (24) : 5205 - 5216
[7] Catalytic direct arylation with aryl chlorides, bromides, and iodides: Intramolecular studies leading to new intermolecular reactions
Campeau, LC
Parisien, M
Jean, A
Fagnou, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (02) : 581 - 590
[8] AZAFLUORANTHENE ALKALOIDS - NEW STRUCTURAL TYPE
CAVA, MP
BUCK, KT
DAROCHA, AI
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (16) : 5931 - &
[9] ALKALOIDS OF ABUTA-IMENE AND ABUTA-RUFESCENS
CAVA, MP
BUCK, KT
NOGUCHI, I
SRINIVASAN, M
RAO, MG
DAROCHA, AI
[J]. TETRAHEDRON, 1975, 31 (15) : 1667 - 1669
[10] A sulfoxide-promoted, catalytic method for the regioselective synthesis of allylic acetates from monosubstituted olefins via C-H oxidation
Chen, MS
White, MC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (05) : 1346 - 1347

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