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Literature DB >> 11846678

Synthesis and properties of spiro nucleosides containing the barbituric acid moiety.

Annabelle Renard¹, Jean Lhomme, Mitsuharu Kotera.

Abstract

The two chiral spiro nucleosides 4 and 5 containing the barbituric acid moiety were efficiently synthesized from optically pure precursors, and their properties were studied. The carbocyclic nucleoside 5 is considerably more stable against ring opening than the deoxyribosyl derivative 4. Both compounds present enhanced hydrogen bonding capacity with diacetyladenosine.

Entities: Chemical

Mesh：

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Year: 2002 PMID： 11846678 DOI： 10.1021/jo016194y

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

6 in total

1. New one-pot synthesis of spiro[furo[2,3-d]pyrimidine-6,5'-pyrimidine]pentaones and their sulfur analogues.

Authors: Mohammad Jalilzadeh; Nader Noroozi Pesyan; Fereshteh Rezaee; Saeed Rastgar; Yaser Hosseini; Ertan Sahin
Journal: Mol Divers Date: 2011-01-29 Impact factor: 2.943

2. Facile and efficient approach for the synthesis of spirocyclopropylbarbiturates and 3-substituted-1,1,2,2-tetracyanocyclopropanes using N-halosulfonamides.

Authors: Ramin Ghorbani-Vaghei; Yaser Maghbooli; Azadeh Shahriari; Jafar Mahmoodi
Journal: Mol Divers Date: 2016-06-13 Impact factor: 2.943

6. Bifunctional thiourea-catalyzed asymmetric [3 + 2] annulation reactions of 2-isothiocyanato-1-indanones with barbiturate-based olefins.

Authors: Jiang-Song Zhai; Da-Ming Du
Journal: Beilstein J Org Chem Date: 2022-01-04 Impact factor: 2.883

6 in total

Synthesis and properties of spiro nucleosides containing the barbituric acid moiety.

1. New one-pot synthesis of spiro[furo[2,3-d]pyrimidine-6,5'-pyrimidine]pentaones and their sulfur analogues.

2. Facile and efficient approach for the synthesis of spirocyclopropylbarbiturates and 3-substituted-1,1,2,2-tetracyanocyclopropanes using N-halosulfonamides.

3. Synthesis and herbicidal activity of 5-(4-hydroxybenzyl)-2-thioxoimidazolidin-4-one esters.

Review 4. Synthesis of Spironucleosides: Past and Future Perspectives.

Review 5. The Bucherer-Bergs Multicomponent Synthesis of Hydantoins-Excellence in Simplicity.

6. Bifunctional thiourea-catalyzed asymmetric [3 + 2] annulation reactions of 2-isothiocyanato-1-indanones with barbiturate-based olefins.