15875-50-0

Upstream product

• 98-03-3 thiophene-2-carbaldehyde 
• 2033-24-1 cycl-isopropylidene malonate 

Downstream Products

• 1246461-46-0 8,8-dimethyl-1,3-diphenyl-4-(2-thienyl)-7,9-dioxa-1,2-diaza-spiro[4.5]dec-2-ene-6,10-dione 
• 1246461-47-1 1-(3-chlorophenyl)-8,8-dimethyl-3-phenyl-4-(2-thienyl)-7,9-dioxa-1,2-diaza-spiro[4.5]dec-2-ene-6,10-dione 

Relevant academic research and scientific papers

2,2-Dimethyl-5-(5-R-2-furfurylidene)-1,3-dioxane-4,6-diones. 4. Synthesis, stereostructures, and properties of thiophene analogs

The reaction of 2-formylthiophenes with Meldrum's acid gave the corresponding thenylidenedioxanediones, which, in contrast to the furfurylidene derivatives, have an s-trans conformation of the mutual orientation of the thiophene ring and the exocyclic double bond. Thenyldioxanediones were synthesized by the selective hydrogenation of the exocyclic double bond.

Rhodium-catalyzed conjugate addition-enantioselective protonation: The synthesis of α,α′-dibenzyl esters

α-Benzyl acrylates, which are conveniently prepared from the corresponding aldehydes, can be employed as substrates in a tandem rhodiumcatalyzed conjugate addition-enantioselective protonation protocol to afford enantiomerically enriched α,α′-dibenzyl est

Organocatalytic kinetic resolution of N-boc-isoxazolidine-5-ones

Easily accessible racemic N-Boc-isoxazolidine-5-ones undergo enantioselective alcoholysis promoted by double hydrogen bond donor amine organocatalysts, resulting in their effective kinetic resolution.

New donor-acceptor stenhouse adducts as visible and near infrared light polymerization photoinitiators

Polymerization photoinitiators that can be activated under low light intensity and in the visible range are being pursued by both the academic and industrial communities. To efficiently harvest light and initiate a polymerization process, dyes with high molar extinction coefficients in the visible range are ideal candidates. In this field, Donor-acceptor Stenhouse Adducts (DASA) which belong to a class of recently discovered organic photochromic molecules still lack practical applications. In this work, a series of DASA-based dyes are proposed as photoinitiators for the free radical polymerization of (meth)acrylates upon exposure to a near infrared light (laser diode at 785 nm).

Boron/zinc exchange for the conjugate arylation of unsaturated Meldrum's acid derivatives

An approach for the conjugate arylation reaction of unsaturated Meldrum's acid derivatives is reported. The reaction takes place through a Boron-Zinc exchange reaction between arylboronic acids and diethylzinc and the subsequent transfer of thus generated reactive aryl groups to the β-position of the double bond of the Meldrum's derivatives. The compounds obtained are valuable synthetic intermediates and can give rise to bioactive molecules such as β,β-disubstituted carboxylic acids and amides.

Enantioselective Ammonium Ylide Mediated One-Pot Synthesis of Highly Substituted γ-Butyrolactones

An ammonium ylide mediated access towards trans-β,γ-disubstituted, all-trans-α,β,γ-trisubstituted, and α,α,β,γ-tetrasubstituted γ-butyrolactones bearing a broad variety of functionalities was developed. Starting from widely accessible benzylidene Meldrum's acid derivatives and α-bromo carbonyl compounds, γ-butyrolactones were obtained in yields between 32–99% with up to excellent diastereoselectivities (>95:5) via a DABCO-mediated [2+1] annulation. Utilization of enantiomerically pure cinchona alkaloid derivatives enables the first asymmetric ammonium ylide mediated method to provide (3R,?4R)-β,γ-disubstituted and (2R,?3R,?4R)-α,β,γ-trisubstituted γ-butyrolactones in moderate to good yields with up to very good enantiomeric ratios (97:3). The scalability of the transformation was proven while determining the absolute configuration. (Figure presented.).

An alternative, practical, and ecological protocol for synthesis of arylidene analogues of Meldrum’s acid as useful intermediates

This paper presents an ecological protocol for Knoevenagel condensation using a catalytic amount of 4,4′-trimethylenedipiperidine as a versatile, efficient, safe, commercially available, inexpensive, and recyclable organocatalyst by a ball-milling process

Challenges in the Development of a Thiol-Based Broad-Spectrum Inhibitor for Metallo-β-Lactamases

Pathogens, expressing metallo-β-lactamases (MBLs), become resistant against most β-lactam antibiotics. Besides the dragging search for new antibiotics, development of MBL inhibitors would be an alternative weapon against resistant bacterial pathogens. Inhibition of resistance enzymes could restore the antibacterial activity of β-lactams. Various approaches to MBL inhibitors are described; among others, the promising motif of a zinc coordinating thiol moiety is very popular. Nevertheless, since the first report of a thiol-based MBL inhibitor (thiomandelic acid) in 2001, no steps in development of thiol based MBL inhibitors were reported that go beyond clinical isolate testing. In this study, we report on the synthesis and biochemical characterization of thiol-based MBL inhibitors and highlight the challenges behind the development of thiol-based compounds, which exhibit good in vitro activity toward a broad spectrum of MBLs, selectivity against human off-targets, and reasonable activity against clinical isolates.

A practical and convenient protocol for the synthesis of (E)-α,β-unsaturated acids

α,β-Unsaturated acids are very useful and versatile reagents in organic synthesis. A novel, practical, and convenient catalytic protocol comprising FeCl3·6H2O (0.5 mol %) and H 2O (1 equiv) in CH3NO2 is described for the rapid synthesis of α,β-unsaturated acids with high E-stereoselectivity under both microwave and conventional heating conditions with high TON and TOF values. This powerful approach efficiently demonstrated the utility of biomass derived aldehydes to build chemical agents used as fuel additives. The method proved to be scalable to gram scale synthesis.

Discovery and preliminary SAR of 5-arylidene-2,2-dimethyl-1,3-dioxane-4,6- diones as platelet aggregation inhibitors

We herein document the discovery of 5-arylidene-2,2-dimethyl-1,3-dioxane-4, 6-diones as a novel family of platelet aggregation inhibitors. The preliminary optimization study enabled us to establish the most salient features of the structure-activity relat