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

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[22] DERIVATIVES OF 2-ALKOXY-5,6-DIHYDRO-ALPHA-PYRAN AS SUBSTRATES IN SYNTHESIS OF MONOSACCHARIDES .8. SYNTHESIS OF BETA-LYXO EPOXIDES FROM 6-SUBSTITUTED 2-ALKOXY-5,6-DIHYDRO-ALPHA-PYRANS
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[23] Synthesis, properties, and oxidizing function of 6-substituted 7,9-dimethylcyclohepta[b]pyrimido[5,4-d]pyrrole-8(7H),10(9H)-dionylium tetrafluoroborates
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[25] PREPARATION OF ALKYL-SUBSTITUTED INDOLES IN THE BENZENE PORTION .11. TOTAL SYNTHESIS OF (6R,8S)-HERBINDOLE-A, (6R,8S)-HERBINDOLE-B, (6R,8S)-HERBINDOLE-C, (6R,8S)-CIS-TRIKENTRIN-A, (6R,8S)-CIS-TRIKENTRIN-B, (6R,8R)-TRANS-TRIKENTRIN-B, AND (6R,8R)-ISO-TRANS-TRIKENTRIN-B - DETERMINATION OF THE ABSOLUTE STRUCTURES OF NATURAL HERBINDOLES AND TRIKENTRINS
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[26] SYNTHESIS OF 6,7-BIS(TRIFLUOROMETHYL)-8-SUBSTITUTED PTERIDINE-2,4(1H,3H)-DIONE (LUMAZINE) HYDRATES FROM 4,5-DIAMINOURACIL HYDROCHLORIDES AND PERFLUOROBUTANE-2,3-DIONE - STABILIZATION OF THE TRANSMOLECULAR COVALENT HYDRATES OF 8-SUBSTITUTED PTERIDINEDIONES BY TRIFLUOROMETHYL GROUPS
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[27] Photochemistry of Tricyclo[5.2.2.02,6]undeca-4,10-dien-8-ones: An Efficient General Route to Substituted Linear Triquinanes from 2-Methoxyphenols. Total Synthesis of (±)-Δ9(12)-Capnellene
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