Versatile synthesis of 6-substituted 8-deazapteridine-2,4-diamines. Formal total synthesis of 8,10-dideazaminopterin

被引：14

作者：

Troschutz, R

Karger, A

机构：

[1] Inst fur Pharmazie/Lebensmittelchem., Universitat Erlangen-Nurnberg, D-91052 Erlangen

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1996年 / 33卷 / 06期

关键词：

D O I：

10.1002/jhet.5570330643

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new synthesis of 4-amino-4-deoxy-8,10-dideazapteroic acid (11d) and 6-substituted and 5,6-anellated 8-deazapteridine-2,4-diamines, 10a, 10d, 25, is described. Starting from keteneaminals 1 or 12 and enaminones 4 or beta-aminoketone 17 the title compounds can be prepared via functional group transformation of 2-amino-3-nitropyridines 5 or nicotinate 13a yielding 3-amino-alpha-picolinonitriles 9 which are cyclocondensed with guanidine.

引用

页码：1815 / 1821

页数：7

共 42 条

[31] Synthesis and in-vitro Antimycobacterial Evaluation of 1-(Cyclopropyl/2,4-difluorophenyl/tert-butyl)-1,4-dihydro-8-methyl-6-nitro-4-oxo-7-(substituted secondary amino)quinoline-3-carboxylic acids
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[32] Synthesis of 8,10-dimethyl-1,10b-dihydro[1,3,5]triazino-[2,1-a]isoindole-2,4,6(3H)-trione by Direct arylation of 1,3,5-triazine-2,4(1H,3H)-dione
Tseitler, T. A.
Zyryanov, G. V.
Kopchuk, D. S.
Kovalev, I. S.
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 50 (06) : 783 - 785
[33] Synthesis of 8,10-dimethyl-1,10b-dihydro[1,3,5]triazino-[2,1-a]isoindole-2,4,6(3H)-trione by Direct arylation of 1,3,5-triazine-2,4(1H,3H)-dione
T. A. Tseitler
G. V. Zyryanov
D. S. Kopchuk
I. S. Kovalev
V. L. Rusinov
O. N. Chupakhin
Russian Journal of Organic Chemistry, 2014, 50 : 783 - 785
[34] APPROACHES TO THE TOTAL SYNTHESIS OF ADRENAL STEROIDS .6. 2,4B-DIMETHYL-7-ETHYLENEDIOXY-1,2,3,4,4AALPHA,4B,5,6,7,8,10,10A-BETA-DODECAHYDROPHENANTHRENE-4-BETA-OL-1-ONE AND RELATED COMPOUNDS
LUKES, RM
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BEYLER, RE
JOHNS, WF
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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (07) : 1707 - 1712
[35] STEREOSPECIFIC SYNTHESIS OF SELECTIVELY C-7-ACETALIZED SUBSTITUTED 4A-BETA-METHYL-3,4,4A,5,6,8A-ALPHA-HEXAHYDRONAPHTHALENE-1(2H),7(8H)-DIONES - A SHORT TOTAL SYNTHESIS OF (+/-)-BETA-EUDESMOL, (+/-)-BETA-SELINENE, AND (+/-)-BETA-DICTYOPTEROL
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JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (23): : 4380 - 4387
[36] 3-Azabicyclo[3.3.1]nonane Derivatives: III. Synthesis of 3-Substituted 9-Acetonyl-1,5-dinitro-3-azabicyclo[3.3.1]-non-6-en-8-ones by Mannich Condensation of the Janovsky σ-Adduct of 2,4-Dinitrophenol with Acetonide Ion
O. V. Leonova
I. V. Shakhkel'dyan
Yu. D. Grudtsyn
Yu. M. Atroshchenko
E. N. Alifanova
S. S. Gitis
P. V. Chudakov
E. G. Nikiforova
N. N. Alekhina
A. Ya. Kaminskii
Russian Journal of Organic Chemistry, 2001, 37 : 395 - 400
[37] 3-Azabicyclo[3.3.1]nonane derivatives:: III.: Synthesis of 3-substituted 9-acetonyl-1,5-dinitro-3-azabicyclo[3.3.1]-non-6-en-8-ones by Mannich condensation of the Janovsky σ-adduct of 2,4-dinitrophenol with acetonide ion
Leonova, OV
Shakhkel'dyan, IV
Grudtsyn, YD
Atroshchenko, YM
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Gitis, SS
Chudakov, PV
Nikiforova, EG
Alekhina, NN
Kaminskii, AY
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 37 (03) : 395 - 400
[38] Synthesis of 11-bromo-9-methyl-6-methylene-3-methylthio-5,6,9,10-tetrahydro-8H-[1,2,4] triazolo[3′,4′:3,4]-pyrazino[1,2-c]pyrimidine-8,10-dione from 4-allyl-1-(3-methyl-2,4-dioxo-1,2,3,4-tetrahydro-6-pyrimidinylcarbonyl) thiosemicarbazide
Myakushkene G.
Vainilavichyus P.
Chemistry of Heterocyclic Compounds, 1999, 35 (1) : 64 - 67
[39] Synthesis of 11-bromo-9-methyl-6-methylene-3-methylthio-5,6,9,10-tetrahydro-8H-[1,2,4]triazolo[3′,4′:3,4]pyrazino[1,2-c]pyrimidine-8,10-dione from 4-allyl-1-(3-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidinyl-6-carbonyl)thiosemicarbazide
Myakushkene, G
Vainilavichyus, P
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1999, (01): : 67 - 70
[40] POLYPHOSPHATE ESTER-CATALYZED CYCLODEHYDRATION OF MONOESTERS OF N-SUBSTITUTED 3-(INDOL-3'-YL)-5-METHYLCYCLOHEX-4-ENE-1,2-DICARBOXYLIC ACIDS - STEREOSELECTIVE SYNTHESIS OF METHYL 9-METHYL-6-OXO-5-TOSYL-5,6,6A-BETA,7-BETA,8,10A-BETA-HEXAHYDROINDENO[2,1-B]INDOLE-7-ALPHA-CARBOXYLATE - X-RAY MOLECULAR-STRUCTURE OF METHYL 5-METHOXY-9-METHYL-6-OXO-5,6,6A-BETA,7-BETA,8,10A-BETA-HEXAHYDROINDENO[2,1-B]-INDOLE-7-CARBOXYLATE
CHENG, KF
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LAI, TF
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (09): : 2487 - 2496

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