Mitsunobu Coupling of Nucleobases and Alcohols:  An Efficient, Practical Synthesis for Novel Nonsugar Carbon Nucleosides

Abstract

A simple facile synthesis of substituted purine derivatives has been developed by using Mitsunobu conditions for an alcohol and a respective nucleobase. A wide range of alcohols produces good to excellent yield (>90%). The resulting purine analogues show good regioselectivity with N-9 substitution as the dominant products in most of the cases. Application of diastereospecific alcohols reveals a complete inversion of the carbon stereogenic center giving a single diastereomer. More than two dozen novel nucleobase derivatives have been prepared in high yield.

Supramolecular Architectures and Magnetic Properties of Self‐Assembled Windmill‐Like Dinuclear Copper(II) Complexes with Purine Ligands

“…[24] The observed Cl···Cl distance is comparable to those found in previously reported compounds in which a chlorine atom is bonded to the C6 atom of the purine base. [25] In contrast, the Cl1 atoms are perpendicularly oriented towards the purine ring of an adjacent dimer, pointing out the nitrogen N21 atom with a distance of 3.2 Å. Previous theoretical work performed on a series of azaaromatic chloride compounds established that this type of Cl···N contact is weakly attractive.…”

Design, synthesis, and biological evaluation of novel thiazolidinediones as PPARγ/FFAR1 dual agonists

“…[42,43] Mitsunobu coupling with the appropriate substituted phenols leading to compounds 15a-g with inversion to the desired (S)-configuration. [44][45][46] These intermediates were condensed under Knoevenagel conditions with 2,4-thiazolidinedione to give benzylidenes 16a-g. Reduction to the saturated 2,4-thiazolidinediones was accomplished using sodium borohydride and catalytic Co/DMG (Scheme 3).…”

Ruthenium‐Catalyzed Oxidative Annulation of 6‐Anilinopurines with Alkynes via CH Activation: Synthesis of Indole‐Substituted Purines/Purine Nucleosides

“…[18] Yield: 0.32 g( 44%);w hite solid;m p9 8-100 8 8C; IR (KBr): n = 3288, 3063, 2981, 1726, 1556, 1496,1 342, 1233, 1058, 942, 860, 761 1, 151.9, 150.9, 146.5, 131.2, 76.8, 68.6, 47.5, 28.6, 25.8 Compound 1o: This was prepared by startingw ith 6-chloro-9-(tetrahydrofuran-2-ylmethyl)-9H-purine by using the same procedure as that for 1a-1m.Y ield:0 .43 g( 74%); white solid;m p1 14-116 8 8C; IR (KBr): n = 3315, 3041,2970,2866,1622,1573,1507,1321,1222,1074,745,647 2, 149.7, 141.8, 138.7, 128.9, 123.4, 120.5, 119.8, 68.4, 46.9, 28.5,2 5.7 9-(4-Bromobenzyl)-6-chloro-9H-purine (precursor of compound 1p): This compound was prepared by the reaction of 4-bromobenzyl bromide with 6-chloropurine according to the literature procedure. [19] Yield:0 .68 g( 65%);w hite solid; mp 136-140 8 8C; IR (KBr): n = 3066, 2920,1589,1557,1329,1172,1067,1011,923,859,754 3, 151.8, 151.3, 144.8, 133.6, 132.5, 131.6, 129.6,1 23.1, 47.3 3, 152.4, 149.7,1 40.3, 138.6, 134.6, 132.3, 129.5, 129.2, 123.8, 122.7, 120.5, 120.3, 46.7 5, 151.5, 150.9, 149.2, 142.3, 138.8, 129.9, 129.3,128.6, 124.4, 122.1, 118.2, 114.6, 55.6, 46.9 5, 151.4, 149.6, 142.5, 139.1, 137.7, 134.0, 129.7, 129.2, 128.2, 124.1, 122.0, 119.2, 46.9, General Procedure for the Synthesis of IndoleAppended Purine Derivatives 3aa-3oa…”