A new method for the preparation of 1,3-dilithiopropyne: an efficient synthesis of homopropargyl alcohols

Cabezas, Jorge A.; Pereira, Alban R.; Amey, Adam

doi:10.1016/s0040-4039(01)01429-0

Cited by 23 publications

(28 citation statements)

References 20 publications

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“…Derivatives 14 and 15 were prepared from alcohol 12, by reaction with NaH and acetylation respectively. Compounds 16 and 17 were synthesized from propargyl bromide, 7, according to Scheme 2 as in [4], and adding NBS and dry ice to the intermediate 8, respectively. …”

Section: Methodsmentioning

confidence: 99%

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Synthesis and Antibacterial Activity of Aromatic Homopropargyl Alcohols

Umaña¹,

Arias²,

Cabezas³

2017

IJOC

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Several aromatic homopropargyl alcohols, and derivatives were prepared by one-pot reaction of 1,3-dilithiopropyne (or its equivalent) with aldehydes and ketones. The antibacterial activity, of alcohols thus prepared, against Gram (+) and Gram (−) bacteria was tested. This activity varies depending upon substitution on the homopropargyl alcohol unit. Apparently, the benzene ring and the free hydroxyl group (or its alcoxide) are needed, in the homopropargyl alcohol unit, to be biologically active.

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Section: Methodsmentioning

confidence: 99%

“…The aim of this work is to report herein the preparation of several homopropargyl alcohols, using procedures depicted in Scheme 2 [4] and Scheme 3 [5], and the determination of its antibacterial activity against both Gram (+) and Gram (−) bacteria.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antibacterial Activity of Aromatic Homopropargyl Alcohols

Umaña¹,

Arias²,

Cabezas³

2017

IJOC

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“…The reaction intermediate thus obtained, was treated with paraformaldehyde overnight (Fig. 3), according to the literature procedure (Cabezas et al, 2001). The volatile by-product obtained (2butyn-1-ol) was removed by Kugelrohr distillation and the residue was purified by column chromatography (ether:hexane) and the product obtained was recrystallized from a mixed ethyl ether:hexanes (1:1) solvent mixture to give colourless block-like crystals.…”

Section: Data Reports Synthesis and Crystallizationmentioning

confidence: 99%

Homopropargyl alcohol 5,5-diphenylpent-2-yne-1,5-diol

2018

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“…The title compound was synthesized by treatment of propargyl bromide with n-BuLi and TMEDA, at À78 C, followed by addition of benzophenone ( Fig. 3), according to a previously reported procedure (Cabezas et al, 2001). It was purified by recrystallization from an ethyl ether:hexanes (1:1) solvent mixture to afford colourless block-shaped crystals.…”

Section: Synthesis and Crystallizationmentioning

confidence: 99%