α-Metalated Isocyanides Research Articles

ChemInform Abstract: Synthesis of Polyisocyanide Compounds via α-Metalation Reactions.

We have used α-metalated isocyanides to build potential ligands with two, three, and four isocyanide groups in a linear array

α-Metalated isocyanides in organic synthesis

α-Alkali-metalated isocyanides, which can be obtained from isocyanides and bases, are both nucleophilic and electrophilic. They can add to polar double bonds, forming heterocycles. They are also synthons for α-metalated primary amines. This paper describes their use in organic synthesis: 1) In heterocyclic synthesis to gives 2-oxazolines, 2-thiazolines, 2-imidazolines, pyrroles, oxazoles, thiazoles, 2-imidazolin-5-ones, 1,3-oxazines and -thiazines. 2) In the field of formylaminomethylenation, transformation of ketones and aldehydes with alkyl isocyanoacetate to formylamino acrylic esters and chain lengthening of ketones to carboxylic acids or carbonitriles with tosyl methylisocyanide. 3) In connection with their use as synthons for primary amines it is demonstrated how they may be used for preparation of 1,2- and 1,3-amino alcohols, 2,3-diaminoalkanoic acids and for synthesis of amino acids.

ChemInform Abstract: SYNTHESES WITH α‐METALATED ISOCYANIDES. 34. SYNTHESIS OF ETHYL 20‐FORMAMIDO‐3‐METHOXY‐19‐NOR‐1,3,5(10),17(20)‐PREGNATETRAEN‐21‐OATE FROM ESTRONE METHYL ETHER WITH ETHYL POTASSIUM ISOCYANOACETATE

Chemischer InformationsdienstVolume 8, Issue 6 Natural Products ChemInform Abstract: SYNTHESES WITH α-METALATED ISOCYANIDES. 34. SYNTHESIS OF ETHYL 20-FORMAMIDO-3-METHOXY-19-NOR-1,3,5(10),17(20)-PREGNATETRAEN-21-OATE FROM ESTRONE METHYL ETHER WITH ETHYL POTASSIUM ISOCYANOACETATE U. SCHOELLKOPF, U. SCHOELLKOPFSearch for more papers by this authorK. HANTKE, K. HANTKESearch for more papers by this author U. SCHOELLKOPF, U. SCHOELLKOPFSearch for more papers by this authorK. HANTKE, K. HANTKESearch for more papers by this author First published: February 8, 1977 https://doi.org/10.1002/chin.197706301Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume8, Issue6February 8, 1977 RelatedInformation

5,6‐Dihydro‐4H‐1,3‐oxazines and γ‐Amino Alcohols from α‐Metalated Isocyanides and Epoxides

5,6‐Dihydro‐4<i>H</i>‐1,3‐oxazines and γ‐Amino Alcohols from α‐Metalated Isocyanides and Epoxides

2‐Unsubstituted Oxazoles from α‐Metalated Isocyanides and Acylating Agents

2‐Unsubstituted Oxazoles from α‐Metalated Isocyanides and Acylating Agents