Thymin-N-Oxide

Klötzer, W.; Herberz, M.

doi:10.1007/bf01185892

Cited by 16 publications

(14 citation statements)

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“…15 The aldehyde 1 was prepared using the reported Vilsmeier conditions (DMF/POCl 3 ) for chloroformylation of 4,6-dihydroxypyrimidine. 16 Functionalization of the two chlorine atoms of aldehyde 1 was carried out with several substituted phenolates. Typically, the nucleophilic substitution of 1a was carried out using 2.2 equiv of phenol and an excess K 2 CO 3 (5-fold) under reflux in THF for 5 h. This yielded the 4,6-disubstituted pyrimidine-5-carbaldehydes 1b-g in excellent yields.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Functionalization of Double Picket Fence Porphyrins Starting from 4,6-Disubstituted Pyrimidine-5-carbaldehydes

et al. 2000

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Section: Resultsmentioning

confidence: 99%

Synthesis and Functionalization of Double Picket Fence Porphyrins Starting from 4,6-Disubstituted Pyrimidine-5-carbaldehydes

et al. 2000

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“…5-Amino-4-dimethylamino-6-mercaptopyrimidine (I) and 4,5-diamino-6-mercaptopyrimidine (V) were produced as described in [5], 5-amino-4-methylamino-6-mercaptopyrimidine (II) as described in [6], 5-amino-4-methoxy-6mercaptopyrimidine (IV) as described in [7], 4-amino-6chloro-5-formylpyrimidine (VI) as described in [8], and 4,6-dichloro-5-formylpyrimidine (VIa) as described in [9].…”

Section: Chemical Methodsmentioning

confidence: 99%

Synthesis and properties of dipyrimido-[4,5-b][5,4-f]-1,4-thiazepine derivatives

Safonova¹,

Nemeryuk²,

Grineva³

et al. 2008

Pharm Chem J

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Derivatives of dipyrimido [4,5-b][5,4-f]-1,4-thiazepine were synthesized and some of their properties were studied.Continuing our reports on the search for biologically active substances among bi-and tricyclic 1,4-thiazine and 1,4-thiazepine systems [1, 4], we present here the synthesis of derivatives of the previously unknown heterocyclic dipyrimido [4,5-b][5,4-f]-1,4-thiazepine system.The interaction of 5-amino-6-mercaptopyrimidines I-V with 5-formyl-6-chloropyrimidine derivatives VI was studied. The primary products of the reaction of 4-dimethylamino-, 4-methylamino-, 4-methoxy-, and 4-methylthio-5amino-6-mercaptopyrimidines (I -IV) with 4-chloro-5-formyl-6-aminopyrimidine (VI) in methanol at 60 -65°C in the presence of an equimolar quantity of KOH were dipyrimidylsulfides VII -X.The IR spectra of compounds VII -X had absorption by an NH 2 group (3200 -3600 cm -1 ) and an aldehyde group (1680 cm -1 ), and the 1 H NMR spectrum showed signals from the CHO group with d 10.2 -10.3 ppm and from protons in the pyrimidine rings at C-2 and C-2¢ with d 7.77 -8.08 ppm, which is consistent with their structures. I, VII: R = N(CH 3 ) 2 ; II, VIII: R = HN(CH 3 ); III, IX: R = OCH 3 ; IV, X: R = SCH 3 ; V: R = NH 2

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confidence: 99%

“…In the present work, we studied the feasibility of using ketones and nitriles in this reaction and investigated the cyclocondensation of ethyl 3,3-diaminoacrylate (1) with 2-fluoro-5-nitroacetophenone (2) [4], three 5-acyl-4,6-dichloropyrimidines (3a-c) [5-7], and two pyrimidinecarbonitriles (4a,b) [8,9].Acetophenone 2 reacts with diaminoacrylate 1 to give only 3-aminoisoquinoline 5. The structure of this product was confirmed by the 1 H NMR spectrum, which is extremely similar to the spectrum of ethyl 3-amino-7-nitroisoquinoline-4-carboxylate (obtained from 2-fluoro-5-nitrobenzaldehyde [1]).…”

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confidence: 99%

Cyclocondensation of ethyl 3,3-diaminoacrylate with aromatic ketones and nitriles containing a labile halogen atom in the ortho position

Yan

Dar’in

Лобанов

et al. 2008

Chem Heterocycl Comp

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The cyclocondensation of aromatic o-halo ketones and o-halo nitriles with ethyl 3,3-diaminoacrylate proceeds as the replacement of the aromatic halogen by the α-carbon atom of the enediamine, while the amino group of the enediamine is bound by the α-carbon atom of the ketone or nitrile group.Keywords: aromatic o-halo ketones and o-halo nitriles, 3,3-diaminoacrylate, cyclocondensation.α-Acylacetamidines, which exist in enediamine form, react with aromatic aldehydes and esters containing a labile halogen atom in the ortho position to give predominantly or exclusively condensed aminopyridines [1][2][3]. In the present work, we studied the feasibility of using ketones and nitriles in this reaction and investigated the cyclocondensation of ethyl 3,3-diaminoacrylate (1) with 2-fluoro-5-nitroacetophenone (2) [4], three 5-acyl-4,6-dichloropyrimidines (3a-c) [5-7], and two pyrimidinecarbonitriles (4a,b) [8,9].Acetophenone 2 reacts with diaminoacrylate 1 to give only 3-aminoisoquinoline 5. The structure of this product was confirmed by the 1 H NMR spectrum, which is extremely similar to the spectrum of ethyl 3-amino-7-nitroisoquinoline-4-carboxylate (obtained from 2-fluoro-5-nitrobenzaldehyde [1]). NOE cross peaks are found in the NOESY correlation spectrum between H-5 and the ethoxy group protons.The nature of the acyl group has the predominant effect on the direction of the reaction for 5-acylpyrimidines 3 with diaminoacrylate 1. Aldehyde 3a (R = H) reacts similarly to its 2-methylsulfanyl analog [2] to give pyridopyrimidine 6, albeit in low yield. The structure of 6 was confirmed by 1 H and 13 C NMR Me O F O 2 N NH 2 NH 2 CO 2 Et O 2 N N NH 2 Me CO 2 Et + 2 1 5

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Thymin-N-Oxide

Cited by 16 publications

References 0 publications

Synthesis and Functionalization of Double Picket Fence Porphyrins Starting from 4,6-Disubstituted Pyrimidine-5-carbaldehydes

Synthesis and Functionalization of Double Picket Fence Porphyrins Starting from 4,6-Disubstituted Pyrimidine-5-carbaldehydes

Synthesis and properties of dipyrimido-[4,5-b][5,4-f]-1,4-thiazepine derivatives

Cyclocondensation of ethyl 3,3-diaminoacrylate with aromatic ketones and nitriles containing a labile halogen atom in the ortho position

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