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Studies on Tetrahydrofuran‐Based Highly O‐Functionalized Alkynes: Applications to Synthesis of Tetrahydrofuranyl‐Polyynes and C‐Nucleoside Analogues
Author(s) -
Reddy P. Venkat,
Bajpai Vikas,
Kumar Brijesh,
Shaw Arun K.
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001442
Subject(s) - chemistry , tetrahydrofuran , cycloaddition , alkyne , amine gas treating , nucleoside , coupling reaction , combinatorial chemistry , catalysis , organic chemistry , medicinal chemistry , stereochemistry , solvent
Abstract The enantiomerically pure tetrahydrofuranylalkynes 17 – 20 were synthesized by using various methods. By utilizing these alkynes, an efficient CuI‐catalysed sp‐sp carbon homo‐coupling protocol in dry DMF without other additives (like amine or base, phosphane and palladium catalyst) has been developed. The method has been applied to the synthesis of symmetrical butadiynyl ( 32 – 37 ), octatetraynyl ( 47 ) and dodecahexaynyl ( 49 ) polyynes. The unsymmetrically substituted diynes 39 , 40 and 41 and triynes 43 and 44 were synthesized by coupling reaction between the newly synthesized bromoalkyne/diynes 38 / 42 and commercially available (trialkylsilyl)acetylenes. Syntheses of the 1,2,3‐triazolyl‐C‐nucleoside analogue 51 and of the ethynyl‐ and butadiynyl‐bridged 1,2,3‐triazolyl‐C‐nucleoside analogues 52 and 53 were performed by 1,3‐dipolar cycloaddition reaction (“click“ chemistry) of their respective alkyne precursors.