Synthesis of the 4,10-Dihydro-3H-pyridazino[1,6-b]isoquinolin-10-one System by a Furan Recyclization Reaction.

ChemInform ◽  
2007 ◽  
Vol 38 (48) ◽  
Author(s):  
Alexander V. Butin ◽  
Artem S. Dmitriev ◽  
Olga N. Kostyukova ◽  
Vladimir T. Abaev ◽  
Igor V. Trushkov
1993 ◽  
Vol 58 (9) ◽  
pp. 2180-2196 ◽  
Author(s):  
Miroslav Otmar ◽  
Ivan Rosenberg ◽  
Milena Masojídková ◽  
Antonín Holý

Further cyclic analogs of the antiviral (S)-9-(3-hydroxy-2-phosphonomethoxypropyl)adenine (I) were prepared: both anomers of [5-(adenin-9-yl)-5-doxy-L-ribofuranosyl]phosphonic acid (α-IId and β-IId) and [5-(adenin-9-yl)-5-doxy-α-L-ribofuranosyl]phosphonic acid (IIe). Recyclization reaction of diethyl (5RS-(3-O-benzyl-1,2-O-isopropylidene-5-O-methanesulfonyl-D-ribofuranos-5-C-yl)phosphonate (IVb) and diethyl (5RS-(3-O-benzyl-1,2-O-isopropylidene-5-O-methanesulfonyl-D-xylofuranos-5-C-yl)phosphonate (IVd) in trifluoroacetic acid led to cyclic aldehydes Va and Vb which were reduced to diethyl α- and β-L-ribofuranosylphosphonates VIb and α-L-xylofuranosylphosphonate VIIb. Conversion to the protected 5-O-tosylates VId and VIId, followed by reaction with adenine and deprotection, afforded the mentioned nucleotide analogs IId and IIe. An attempt to prepare L-pentofuranosylphosphonates Vc and XIII, suitable for the synthesis of nucleotide analogs of 3-deoxy-L-erythro and L-xylo configuration (IIf and IIg, respectively) by the recyclization reaction of the corresponding 5-O-methanesulfonyl derivatives IVf and XIIb failed. In this case, anhydro derivatives IXa, XVa and XVIa were isolated and identified.


Synthesis ◽  
2007 ◽  
Vol 2007 (14) ◽  
pp. 2208-2214 ◽  
Author(s):  
Alexander Butin ◽  
Artem Dmitriev ◽  
Olga Kostyukova ◽  
Vladimir Abaev ◽  
Igor Trushkov

ChemInform ◽  
2010 ◽  
Vol 24 (44) ◽  
pp. no-no
Author(s):  
A. V. BUTIN ◽  
V. E. ZAVODNIK ◽  
V. G. KUL'NEVICH

1982 ◽  
Vol 18 (5) ◽  
pp. 540-540
Author(s):  
Yu. M. Yutilov ◽  
I. A. Svertilova

2003 ◽  
Vol 13 (5) ◽  
pp. 232-233 ◽  
Author(s):  
Fanusa A. Gimalova ◽  
Oleg A. Gavrilov ◽  
Denis G. Golovanov ◽  
Vladimir K. Mavrodiev ◽  
Mansur S. Miftakhov

Tetrahedron ◽  
2007 ◽  
Vol 63 (2) ◽  
pp. 474-491 ◽  
Author(s):  
Alexander V. Butin ◽  
Sergey K. Smirnov ◽  
Tatyana A. Stroganova ◽  
Wolfgang Bender ◽  
Gennady D. Krapivin

Tetrahedron ◽  
2007 ◽  
Vol 63 (38) ◽  
pp. 9437-9447 ◽  
Author(s):  
Artem S. Dmitriev ◽  
Vladimir T. Abaev ◽  
Wolfgang Bender ◽  
Alexander V. Butin

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