1‐Aryl‐3‐(dimethylamino)propenones: Strong Proton Acceptors for Hydrogen Bonds

Pleier, Anna-Katharina; Herdtweck, Eberhardt; Mason, Sax A.; Thiel, Werner R.

doi:10.1002/ejoc.200390086

Cited by 13 publications

(6 citation statements)

References 22 publications

(13 reference statements)

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“…Pyrazoles bound to an aromatic ring at their 3-positions are obtained in high yields through ring-closure reactions between hydrazine and 1-aryl-3-(dimethylamino)prop-2-en-1-ones. [26] To follow this route (Scheme 3), enantiomerically pure dimethyl (R)-1,1Ј-binaphthyl-2,2Ј-dicarboxylate [(R)-10] [27] was treated with NaH/DMSO [28] to give (R)-2,2Ј-bis-…”

Section: Resultsmentioning

confidence: 99%

“…[29] The acetyl group of (R)-12 gives typical resonances in the 1 H NMR (δ =2.09 ppm) and 13 C{ 1 H} NMR spectrum (201.4, 29.4 ppm), as well as a characteristic absorption in the IR spectrum (ν CO = 1689 cm -1 ). Treatment of compound (R)-12 with dimethylformamide dimethyl acetal (DMFDMA) [26] generates…”

Section: Resultsmentioning

confidence: 99%

“…Compound (R)-13 can be identified spectroscopically by the typical resonances of the 3-(dimethylamino)-prop-2-enoyl units: because of the hindered rotation around the CH-N bond [26] two broad resonances are found for the terminal methyl groups both in the 1 H (2.83, 2.15 ppm) and in the 13 C{ 1 H} NMR spectrum (44.5, 36.4 ppm). The inclusion of the nitrogen lone pair in the π system of the side chain increases the electron density at the carbonyl C atom and leads to low-field shifting of the CO resonance in the 13 C{ 1 H} NMR spectrum.…”

Section: Resultsmentioning

confidence: 99%

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A Series of Novel N,N‐Donor Ligands with Binaphthyl Backbones

et al. 2009

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Chiral ligands with the 1,1′‐binaphthyl unit as the backbone play an important role in enantioselective catalysis. In this paper we present the synthesis and characterization of three novel azole‐functionalized 1,1‐binaphthyl derivatives. These systems are accessible from commercially available starting materials in not more than four steps. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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A Series of Novel N,N‐Donor Ligands with Binaphthyl Backbones

et al. 2009

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“…It is interesting to note that the alkylation does not occur in the case of the enaminone intermediate derived from 2‐hydroxyacetophenone 1 b ( 4 b , Table ). This can be explained by considering the difficulty in abstracting the proton of the aromatic OH group due to the strong intramolecular H‐bonding with the neighboring oxygen atom of the oxo functionality …”

Section: Figurementioning

confidence: 99%

Metal‐Free Route for the Synthesis of 4‐Acyl‐1,2,3‐Triazoles from Readily Available Building Blocks

Thomas

Goyvaerts

Liekens

et al. 2016

Chemistry A European J

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Functionalized 1,2,3-triazole heterocycles have been known for a long time and hold an extraordinary potential in diverse research areas ranging from medicinal chemistry to material science. However, the scope of therapeutically important 1-substituted 4-acyl-1H-1,2,3-triazoles is much less explored, probably due to the lack of synthetic methodologies of good scope and practicality. Here, we describe a practical and efficient one-pot multicomponent reaction for the synthesis of α-ketotriazoles from readily available building blocks such as methyl ketones, N,N-dimethylformamide dimethyl acetal, and organic azides with 100 % regioselectivity. This reaction is enabled by the in situ formation of an enaminone intermediate followed by its 1,3-dipolar cycloaddition reaction with an organic azide. We effectively utilized the developed strategy for the derivatization of various heterocycles and natural products, a protocol which is difficult or impossible to realize by other means.

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“…Crystallization from wet acetone gives the trihydrate of this compound wherein the water molecules act as proton donors and acceptors in the expected two‐dimensional hydrogen bonded network. However, cocrystallization with larger proton donors like hydroquinone or 4,4′‐dihydroxybiphenyl gives linear structures wherein only two of the three 3‐dimethylaminoprop‐2‐en‐1‐one side chains are engaged in hydrogen bonding, presumably this is due to steric reasons 4a. By following something like a crystal engineering strategy, the steric problems can be overcome by changing the core from a planar 1,3,5‐trisubstituded benzene into a pyramidal arrangement like it is, for example, realized in triarylphosphanes.…”

Section: Introductionmentioning

confidence: 99%

P309: Fetal echocardiography results in twins at the referral center

Respondek‐Liberska

Grzesiak

Jakubowski

2003

Ultrasound Obstet Gynecol

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Objective: Retrospective analysis of the spectrum of fetal aortic valve stenosis with completed neonatal follow-up. Methods: Fetal echocardiograms of 12 fetuses with aortic stenosis (AS) were analyzed. Mean gestational age at the time of diagnosis was 29.6 weeks. Results: In all 12 cases critical AS has been detected. The left ventricle was estimated as a small in three cases, in 7 cases as enlarged and hypokinetic LV (SF < 28%) and in the next two cases the LV was well formed. In 6 AS cases endocardial fibroelastosis has been detected. Six fetuses presented mitral valve insufficiency, in three cases with small LV mitral valve stenosis was diagnosed. Cardiomegaly occured in 7 cases, including 5 cases with HA/CA > 0.5. Hypoplastic aorta has been detected in 2 cases and in one coartaction of the aorta. Retrograde flow in aortic arch and poor left ventricular function was diagnozed in ten cases. In 2 fetuses extracardiac malformations were present: hydrocephalus and pylorostenosis. In 83% of the cases CS had been performed and 17% were delivered vaginally (2 demises in utero). Four neonates had been qualified to percutaneous balloon valvuloplasty, in three cardiac surgery had been performed. Three neonates with AS (25%) survived -two after valvuloplasty (one of them required also cardiac surgery) and one after Norwood procedure. Conclusions: 1. Poor prognostic factors for neonates with critical fetal SA were as follow: small LV, retrograde flow in aortic arch, hypoplastic asceding aorta, coartaction of the aorta and poor left ventricular function and presence of extracardiac anomalies. 2. Neonates who survived fetal SA had large left ventricle (also with endocardial fibroelastosis) or almost normal growth of LV. P309Fetal echocardiography results in twins at the referral center M. Respondek-Liberska, M. Grzesiak and K. Janiak Research Institute Polish Mother's Memorial Hosp., PolandAim: The aim of the study was a retrospective analysis of fetal echo in twins. Material: 81 pregnancies with 162 fetuses and completed followup. Mean age of pregnant women was 29.1 years, mean fetal age at the time of targeted fetal echocardiography was 25 wks, mean neonatal birth weight was 1754, Apgar 6. There were 43 deaths (43/162 = 26.5%), including 17 in utero and in 26 after delivery. Results: In 162 twin fetuses, the abnormal fetal echocardiography findings were present in 51 fetuses (31.5%). There were: 22 fetuses with TTTS (43.1%), 6 conjoined twins (11.8%), 4 pregnancies with acardiac twin (8 ''twins'') (15.6%), 6 fetuses with CHD (11.8%) and 9 fetuses (17.7%) with arrhythmias. In 22 fetuses with TTTS the most common anomaly was fetal cardiomegaly (11/22) and tricuspid valve regurgitation -TR (11/22). All conjoined twins had common hearts with different anatomy. The most common anomaly in ''normal'' twin with acardiac cotwin was cardiomegaly and TR. There were 6 fetuses (6/51-17.7%) with CHD: 3 × VSD, 1 × HLHS, 1 × AV Canal and 1 × Truncus arteriosus. There were 9 fetuses (9/51-17.7%) with arrhythmias, including 8 fetuses with...

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1‐Aryl‐3‐(dimethylamino)propenones: Strong Proton Acceptors for Hydrogen Bonds

Cited by 13 publications

References 22 publications

A Series of Novel N,N‐Donor Ligands with Binaphthyl Backbones

A Series of Novel N,N‐Donor Ligands with Binaphthyl Backbones

Metal‐Free Route for the Synthesis of 4‐Acyl‐1,2,3‐Triazoles from Readily Available Building Blocks

P309: Fetal echocardiography results in twins at the referral center

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