Dehydrocyclization of 4-Amino-5-arylamidopyrimidines to Purines with Polyphosphoric Acid<sup>1a,b</sup>

Fu, S.-C. J.; Chinoporos, Efthimios; Terzian, H.

doi:10.1021/jo01017a049

Cited by 27 publications

(14 citation statements)

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“…Owing to the fact that compounds 2a-c contain acylamine residues and a thioxo group in vicinal positions, intramolecular cyclization under the action of phosphorus pentasulfide or polyphosphoric acid remains a possibility. Similar reactions are well known in syntheses of thiazolopyrimidine derivatives [10][11][12][13]. It should be noted that on carrying out this reaction it is also possible to expect the formation of tricyclic structures 4a-c with a purine fragment (see analogies in [14][15][16][17][18]).…”

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confidence: 52%

Synthesis and structure of a new heterocyclic system – 7,8-dihydroimidazo- [1,2-c][1,3]thiazolo[4,5-e]pyrimidine

Kozachenko

Шаблыкин

Василенко

et al. 2011

Chem Heterocycl Comp

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Keywords: 8-aroylamino-1,2,3,7-tetrahydroimidazo[1,2-c]pyrimidines, phosphorus pentasulfide, polyphosphoric acid, triethyl orthoformate, heterocyclization.N-(2-Amino-1-imidazolidin-2-ylidene-2-thioxoethyl)arylamides 1 (see Scheme), synthesized from available 2-acylamino-3,3-dichloroacrylonitriles [1], were used previously to obtain the new heterocyclic system 4,5,7,It was shown in the present study that compounds 1 may be applied in the synthesis of one more new heterocyclic system 3, viz. 7,8-dihydroimidazo[1,3-c][1,3]thiazolo[4,5-e]pyrimidine. In difference to the preparation of the 7,8-dihydroimidazo[1,2-c][1,3]oxazolo[4,5-e]pyrimidine system in [3], in the present case a different method of design of the tricyclic heterocyclic system was used, the key stage of which was not the formation of the pyrimidine ring but annelation of the five-membered ring to a tetrahydroimidazo[1,2-c]pyrimidine fragment. First, compounds 1a-c were condensed with triethyl orthoformate with the formation of the previously unknown 8-aroylamino-7-thioxo-1,2,3,7-tetrahydroimidazo[1,2-c]pyrimidines 2a-c (Scheme and Table 1).Similar heterocyclizations of compounds with the characteristic fragment NH C C C(S)NH 2 were described previously in [4,5], but the products of such reactions are as a rule monocyclic derivatives of pyrimi-

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confidence: 52%

Synthesis and structure of a new heterocyclic system – 7,8-dihydroimidazo- [1,2-c][1,3]thiazolo[4,5-e]pyrimidine

Kozachenko

Шаблыкин

Василенко

et al. 2011

Chem Heterocycl Comp

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“…The structures of these compounds were proved by elemental analyses, uv spectral data which were similar to those of 8-arylpurines 16 except the compounds 11c and 11f which exhibit a hypsochromic shift due to the planarity of 8-aryl with the xanthine ring.…”

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confidence: 87%

“…3,9-dimethylxanthines has been prepared by various methods. [10][11][12][13] 8-Arylpurines have been synthesized either by dehydrocyclization of 4-amino-5-arylamidopyrimidines with phosphoryl chloride, 14,15 phosphoric acid 16 and by dry heating, 17 or by cyclization of Schiffs base analogues using ferric chloride, 18 nitrobenzene, 19 or bisulfite adduct of aldehydes. 20 We report herein the synthesis of some purine analogues, namely 3,9-dimethyl-, and 8-aryl-3,9-dimethylxanthines.…”

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confidence: 99%

A Novel Synthesis of 3,9-Dialkyl and 8-Aryl-3,9-dimethylxanthines

2002

Bulletin of the Korean Chemical Society

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Several compounds of 3,9-dialkylxanthines were prepared from 1-methyl-6-chlorouracil via nucleophillic reactions with different aliphatic amines, followed by nitrosation, reduction, formaylation and finally dehydrocyclization. On the other hands, a series of 8-aryl-3,9-dimethylxanthines were synthesized by dehydrocyclization of 5-arylamido-1-methyl-6-methylaminouracils either by fussion or oxidation of 5-arylidineamino-1-methyl-6-methylaminouracils using sodium periodate. Phosphoryl chloride was found to be uneffective reagent for dehydrocyclization that, gave another products from 1,3-oxazolo [5,4-d] pyrimidines.

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“…Purine derivatives have been synthesized by the reaction of dehydrocyclization of 4‐amino‐5‐arylamidopyrimidine with polyphosphoric acid , cyclocondensation of aminoimidazole with methyl‐2‐phenylthioethyl carbamate in the presence of a base , and amino‐pyrimidine, substituted acid with ultrasonic irradiation .…”

Section: Introductionmentioning

confidence: 99%

An Alternative Regioselective Approach for the Synthesis of Highly Functionalized Derivatives of Pyrazolo[5,1‐b]purine Scaffold

Sheikhi‐Mohammareh

Shiri

2018

Journal of Heterocyclic Chem

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A straightforward approach for the regioselective synthesis of highly functionalized pyrazolo[5,1‐b]purine from the annulation of 6‐bromo‐3‐cyano‐2‐(ethylthio)‐5‐methyl‐7‐oxo‐6,7‐dihydropyrazolo[1,5‐a]pyrimidine with thiourea as a bisnucleophilic reagent under reflux condition in CH3CN in the presence of Et3N has been developed. The N‐alkylation of the synthesis compound was also accomplished. The true regioisomer was determined by 2D‐NOESY NMR spectroscopy, as well.

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Dehydrocyclization of 4-Amino-5-arylamidopyrimidines to Purines with Polyphosphoric Acid^1a,b

Cited by 27 publications

References 1 publication

Synthesis and structure of a new heterocyclic system – 7,8-dihydroimidazo- [1,2-c][1,3]thiazolo[4,5-e]pyrimidine

Synthesis and structure of a new heterocyclic system – 7,8-dihydroimidazo- [1,2-c][1,3]thiazolo[4,5-e]pyrimidine

A Novel Synthesis of 3,9-Dialkyl and 8-Aryl-3,9-dimethylxanthines

An Alternative Regioselective Approach for the Synthesis of Highly Functionalized Derivatives of Pyrazolo[5,1‐b]purine Scaffold

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Dehydrocyclization of 4-Amino-5-arylamidopyrimidines to Purines with Polyphosphoric Acid1a,b

Cited by 27 publications

References 1 publication

Synthesis and structure of a new heterocyclic system – 7,8-dihydroimidazo- [1,2-c][1,3]thiazolo[4,5-e]pyrimidine

Synthesis and structure of a new heterocyclic system – 7,8-dihydroimidazo- [1,2-c][1,3]thiazolo[4,5-e]pyrimidine

A Novel Synthesis of 3,9-Dialkyl and 8-Aryl-3,9-dimethylxanthines

An Alternative Regioselective Approach for the Synthesis of Highly Functionalized Derivatives of Pyrazolo[5,1‐b]purine Scaffold

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Dehydrocyclization of 4-Amino-5-arylamidopyrimidines to Purines with Polyphosphoric Acid^1a,b