777. A novel reduction of nitriles to aldehydes

Backeberg, O. G.; Staskun, Benjamin

doi:10.1039/jr9620003961

Cited by 80 publications

(31 citation statements)

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“…Further reactions were similar to the route of Bergmann and Gericke 8 (addition of 2-pyridinol to the epoxides with catalytic amounts of pyridine in refluxing ethanol). Unfortunately it was necessary to separate the resulting mixtures of the pyridones (9, 10) and the (pyridyloxy)-chromanols (11,12) by silica gel chromatography. To avoid this procedure we boiled the components with potassium carbonate in toluene, and the trans-configurated pyridones were the only reaction products in almost quantitative yield.…”

Section: Chemistrymentioning

confidence: 99%

6-Substituted Benzopyrans as Potassium Channel Activators: Synthesis, Vasodilator Properties, and Multivariate Analysis

et al. 1999

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During the last 10 years compounds have been discovered which can activate or block KATP channels. In particular, K channel activators (KCA) have been found to be smooth muscle relaxants with their main utility in hypertension and bronchodilation. In this paper we describe the synthesis of new KCA of the benzopyran type with a fixed 4-substituent and a systematic variation in the 6-position. The relaxant potency in rat aorta and trachea was used for biological characterization of the benzopyrans. In both biological test systems, they exhibit potency ranges of more than 3 log units. Structure-activity relationships are investigated by principal component analysis (PCA) and partial least-squares (PLS) analysis. Most striking outliers in an initial PLS analysis of the entire database were the unsubstituted 6-H compound 13 as well as 34 and 35. For the remaining set of 31 compounds, a 3-component PLS model explains the variance in biological activity to 81% in the aortic and to 82% in the tracheal test system. 6-Substituents influence affinity by a direct (presumably dipolar) interaction with the receptor site. According to the 2D-plot of the partial PLS weights, a strong electronegativity as well as high values for the integy moment and for the heat of formation in water dominate the first component; low values for substituent size (as defined by globularity or surface) are in addition favorable for high potency. High lipophilicity and low minimum energies of interaction dominate the second component. Chemical descriptors for the biological potency of the test set in rat aorta and rat trachea are very similar according to the almost identical projection of the Y-variables onto the X-component space.

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Section: Chemistrymentioning

confidence: 99%

6-Substituted Benzopyrans as Potassium Channel Activators: Synthesis, Vasodilator Properties, and Multivariate Analysis

et al. 1999

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“…Conditions for the selective conversion of the nitrile group into an aldehyde were sought that left the carbamate and ester protecting groups intact. When separate reductions of 6a and 6b were carried out with Raney nickel in the presence of sodium hypophosphite (Scheme ),26 the corresponding aldehydes 7a and 7b were obtained in 73 and 91 % yields, respectively. Two possible routes to convert aldehydes into nitronyl nitroxides have been previously reported.…”

Section: Resultsmentioning

confidence: 99%

A Quaternary Nitronyl Nitroxide α‐Amino Acid: Synthesis, Configurational and Conformational Assignments, and Physicochemical Properties

et al. 2014

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To expand the presently extremely limited repertoire of known nitronyl nitroxide α‐amino acids, we report here the synthesis of a novel, conformationally constrained, quaternary, chiral residue, Aic(CN), and its subsequent conversion into a blue‐colored, imidazolinyl nitronyl nitroxide‐bearing α‐amino acid, Aic(NN). Deprotection and peptide coupling reactions were examined. The configurational assignment of Aic(NN) was achieved by X‐ray crystallographic analysis of an appropriate tripeptide. This latter investigation, accompanied by an IR absorption conformational analysis, strongly supports the view that the Aic(NN) residue is an efficient peptide turn former. Numerous spectroscopic and magnetic properties of its derivatives and the tripeptide are also described. Of particular relevance for future applications are its UV/Vis absorption, NMR, and EPR signatures.

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“…Although chemoselective reduction of the cyano moiety proved to be highly difficult under a variety of conditions, it could be chemoselectively reduced to aldehyde 15 with Raney Ni W4 in the presence of NaPH 2 O 2 /H 2 O/acetic acid/ pyridine. [9] In the final step, the deprotection of the PMP group was examined under various oxidation or reduction conditions [CAN,O 3 , (NH 4 ) 2 S 2 O 8 /AgNO 3 , Na/liqu. NH 3 , etc].…”

Section: Synthesis Of Monopyrrole Aldehydementioning

confidence: 99%

A New Method for the Synthesis of Multisubstituted Pyrroles of Biological Interest by Double Nucleophilic Addition to α,β‐Unsaturated Imines

et al. 2009

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Double nucleophilic addition reactions of dialkoxy ketenesilyl acetals proceeded with α,β‐unsaturated imines to give 1,4‐ and 1,2‐double addition products, and their subsequent transformations afforded multisubstituted pyrroles in good yields. Application of this procedure to the synthesis of an imidazole glycerol phosphate dehydratase inhibitor (IGPDI), a physiologically active 2,3,5‐trisubstituted pyrrole, is also described.

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777. A novel reduction of nitriles to aldehydes

Cited by 80 publications

References 0 publications

6-Substituted Benzopyrans as Potassium Channel Activators: Synthesis, Vasodilator Properties, and Multivariate Analysis

6-Substituted Benzopyrans as Potassium Channel Activators: Synthesis, Vasodilator Properties, and Multivariate Analysis

A Quaternary Nitronyl Nitroxide α‐Amino Acid: Synthesis, Configurational and Conformational Assignments, and Physicochemical Properties

A New Method for the Synthesis of Multisubstituted Pyrroles of Biological Interest by Double Nucleophilic Addition to α,β‐Unsaturated Imines

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