The use of acetylenic aldehydes in Baylis–Hillman reactions: synthesis of versatile allyl propargyl alcohols

Silicon- and germanium-substituted propynals as ambident electrophiles for the design of new heterocycles and polyfunctional acetylenes

“…in DMSO, leading to allylic propargylic alcohols, has been described later. 77 2.3. Reaction of heteroatomic propynals with S,N binucleophiles.…”

First Stereoselective Total Synthesis of Gallicynoic Acids G and H

“…Colorless liquid. HPLC (Chiral Pak-IC, 3% i PrOH/hexane, flow rate 1 ml/min, 210 nm): t R (major) 9.922, t R (minor) 10 2 (0.02 ml, 0.33 mmol) in dry CH 2 Cl 2 (2 ml), DMSO (0.04 ml, 0.67 mmol) was added at À 788 and stirred for 30 min at À 788, followed by the addition of 17 (0.10 g, 0.22 mmol) in CH 2 Cl 2 (1.5 ml). The mixture was stirred for 1 h at À 788, Et 3 N (0.18 ml, 1.35 mmol) was added at À 788, and stirring was continued for another 15 min.…”

“…Recently, gallicynoic acids G (1) and H (2) were isolated from a culture of the basidiomycete Coriolopsis gallica [9]. Our interest in chiral propynyl alcohols and allyl propynyl alcohols dates back in time and recently led to their synthesis via BaylisÀHillman reaction [10] of corresponding propynals. These multifunctional products are versatile synthons in the synthesis of bioactive natural products [11].…”

A facile one-pot synthesis of novel 1-substituted 2-(8-hydroxyquinolin-5-yl)-1,5,6,7-tetrahydro-6,6-dimethyl- 4H-indol-4-one derivatives

“…12 In recent years, 1,4-diazabicyclo[2.2.2]octane (DABCO) has emerged as a promoter for various organic reactions. [13][14][15][16][17] DABCO is an organic base that can act as a nucleophile. In view of this, and as part of our work on multi-component reactions, [18][19][20][21][22] we here report a simple, practical, and generally three-component reaction for the synthesis of novel indole derivatives by one-pot three-component reaction of 5-chloroacetyl-8-hydroxyquinoline, alkyl-, aryl-and heteroaryl-amines, and dimedone; the reaction is catalyzed by DABCO.…”