General approach to 6-tosyl-2,3,4,5-tetrahydro-1H-1,3-diazepin-2-ones via nucleophile-mediated ring expansion of tetrahydropyrimidines
作者： Anastasia A. Fesenko , Marcus L. Tullberg , Anatoly D. Shutalev
DOI: 10.1016/J.TET.2009.01.015
关键词:
摘要: A general six-step approach to 6-tosyl-2,3,4,5-tetrahydro-1H-1,3-diazepin-2-ones has been developed. The key step involves a ring expansion reaction of 4-mesyloxymethyl- or 4-tosyloxymethyl-5-tosyl-1,2,3,4-tetrahydropyrimidin-2-one mediated by nucleophilic reagents.
elsevier.com
sci-hub.se 参考文章(18)
John Ashby, D. Griffiths, Some ring expansion–ring contraction reactions of ethyl 4-chloromethyl-1,2,3,4-tetrahydro-6-methyl-2-oxopyrimidine-5-carboxylate J. Chem. Soc., Chem. Commun.. pp. 607- 608 ,(1974) , 10.1039/C39740000607
V. E. MARQUEZ, K. V. B. RAO, J. V. SILVERTON, J. A. KELLEY, A RING EXPANSION APPROACH TO 1,3-DIAZEPIN-2-ONE NUCLEOSIDES Journal of Organic Chemistry. ,vol. 49, pp. 912- 919 ,(1984) , 10.1002/CHIN.198432328
Brian Gregory, Eric Bullock, Teng-Song Chen, Intramolecular Michael-type additions. IV: Synthesis of 2-azabicyclo[3.2.1]oct-3-enes from 4-chloroalkyl-1,4-dihydropyridines Canadian Journal of Chemistry. ,vol. 63, pp. 843- 848 ,(1985) , 10.1139/V85-140
Anastasia A. Fesenko, Anatoly D. Shutalev, Diastereoselective synthesis of 5-benzylthio- and 5-mercaptohexahydropyrimidin-2-ones Tetrahedron Letters. ,vol. 48, pp. 8420- 8423 ,(2007) , 10.1016/J.TETLET.2007.09.173
Christian Klein, Günter Schulz, Wolfgang Steglich, Umwandlung von ω‐Guanidino‐ und ω‐Ureido‐α‐aminosäuren in α‐Ketosäuren und deren heterocyclische Folgeprodukte European Journal of Organic Chemistry. ,vol. 1983, pp. 1623- 1637 ,(1983) , 10.1002/JLAC.198319830917
Eric Bullock, Roger A. Carter, Regina M. Cochrane, Brian Gregory, Douglas C. Shields, The synthesis of 1,3-diazepine derivatives by the ring expansion of alkyl 4-chloromethyl-1,2,3,4-tetrahydro-6-methyl-2- oxopyrimidine-5-carboxylates Canadian Journal of Chemistry. ,vol. 55, pp. 895- 905 ,(1977) , 10.1139/V77-124
A. D. Shutalev, V. A. Kuksa, UTILIZATION OF THE AMIDOALKYLATION REACTION IN THE SYNTHESIS OF HYDROGENATED PYRIMIDINE-2-THIONES Chemistry of Heterocyclic Compounds. ,vol. 33, pp. 91- 95 ,(1997) , 10.1007/BF02290753
David A. Claremon, David E. McClure, James P. Springer, John J. Baldwin, Synthesis of 4,5-dihydroazepine-3,6-dicarboxylate derivatives by stereoselective ring expansion-nucleophilic addition to 4-.alpha.-chloroalkyl-1,4-dihydropyridine-3,5-dicarboxylates Journal of Organic Chemistry. ,vol. 49, pp. 3871- 3874 ,(1984) , 10.1021/JO00194A055
Jinfa Du, Kyoichi A. Watanabe, Facile Preparation of α‐Acyloxyacetaldehyde, a Versatile Intermediate in the Synthesis of Antiviral Nucleosides Synthetic Communications. ,vol. 34, pp. 1925- 1930 ,(2004) , 10.1081/SCC-120037904
John Ashby, David Griffiths, Some base-catalysed ring expansion and ring expansion–ring contraction reactions of ethyl 4-chloromethyl-1,2,3,4-tetrahydro-6-methyl-2-oxopyrimidine-5-carboxylate J. Chem. Soc., Perkin Trans. 1. ,vol. 6, pp. 657- 662 ,(1975) , 10.1039/P19750000657