Studies on the reactivity of α-cyano-α-isocyanoalkanoates - versatile synthons for the assembly of imidazoles
The reactivity and the synthetic potential of α-cyano-α-isocyanoalkanoates 2 were investigated. Interestingly, reaction of 2 with alkoxides gave (alkoxy)(alkyl)imidazoles 5, whereas the analogous thiolates led to different products, namely substituted 4H-imidazoles 7, together with compounds 6, whic...
Gespeichert in:
| Hauptverfasser: | , |
|---|---|
| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
1999
|
| In: |
Helvetica chimica acta
Year: 1999, Jahrgang: 82, Heft: 6, Pages: 909-918 |
| ISSN: | 1522-2675 |
| DOI: | 10.1002/(SICI)1522-2675(19990609)82:6<909::AID-HLCA909>3.0.CO;2-T |
| Online-Zugang: | Verlag, kostenfrei registrierungspflichtig, Volltext: http://dx.doi.org/10.1002/(SICI)1522-2675(19990609)82:6<909::AID-HLCA909>3.0.CO;2-T Verlag, kostenfrei registrierungspflichtig, Volltext: http://onlinelibrary.wiley.com/doi/10.1002/(SICI)1522-2675(19990609)82:6<909::AID-HLCA909>3.0.CO;2-T/abstract 
|
| Verfasserangaben: | by Marco Bergemann and Richard Neidlein |
MARC
| LEADER | 00000caa a2200000 c 4500 | ||
|---|---|---|---|
| 001 | 155767647X | ||
| 003 | DE-627 | ||
| 005 | 20230426153704.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 170428s1999 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1002/(SICI)1522-2675(19990609)82:6<909::AID-HLCA909>3.0.CO;2-T |2 doi | |
| 035 | |a (DE-627)155767647X | ||
| 035 | |a (DE-576)487676475 | ||
| 035 | |a (DE-599)BSZ487676475 | ||
| 035 | |a (OCoLC)1340973241 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rda | ||
| 041 | |a eng | ||
| 084 | |a 32 |2 sdnb | ||
| 100 | 1 | |a Bergemann, Marco |e VerfasserIn |0 (DE-588)1130894274 |0 (DE-627)885252195 |0 (DE-576)487676394 |4 aut | |
| 245 | 1 | 0 | |a Studies on the reactivity of α-cyano-α-isocyanoalkanoates - versatile synthons for the assembly of imidazoles |c by Marco Bergemann and Richard Neidlein |
| 246 | 3 | 3 | |a Studies on the reactivity of alpha-cyano-alpha-isocyanoalkanoates - versatile synthons for the assemby of imidazoles |
| 264 | 1 | |c 1999 | |
| 300 | |a 9 | ||
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a Computermedien |b c |2 rdamedia | ||
| 338 | |a Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Gesehen am 28.04.2017 | ||
| 520 | |a The reactivity and the synthetic potential of α-cyano-α-isocyanoalkanoates 2 were investigated. Interestingly, reaction of 2 with alkoxides gave (alkoxy)(alkyl)imidazoles 5, whereas the analogous thiolates led to different products, namely substituted 4H-imidazoles 7, together with compounds 6, which formed by addition of thiolate to the isocyano group. Primary amines reacted, on one hand, in the same manner as thiolates to form of 4H-imidazoles 10, and, on the other hand, cleavage of the molecule to the proposed unstable aminoimidazole 8 and the carbamate 9 was observed. Secondary amines add selectively to the isocyano group to form compounds 11. Like simple isocyanides, α-cyano-α-isocyanoalkanoates 2 can be subjected to [4+1] cycloadditions and multicomponent reactions of the Passerini type. Mechanisms for the described reactions are discussed. | ||
| 700 | 1 | |a Neidlein, Richard |d 1930-2012 |e VerfasserIn |0 (DE-588)1012574288 |0 (DE-627)699719496 |0 (DE-576)345624564 |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Helvetica chimica acta |d New York, NY : Wiley-VCH, 1918 |g 82(1999), 6, Seite 909-918 |h Online-Ressource |w (DE-627)269534563 |w (DE-600)1475013-2 |w (DE-576)077884698 |x 1522-2675 |7 nnas |a Studies on the reactivity of α-cyano-α-isocyanoalkanoates - versatile synthons for the assembly of imidazoles |
| 773 | 1 | 8 | |g volume:82 |g year:1999 |g number:6 |g pages:909-918 |g extent:9 |a Studies on the reactivity of α-cyano-α-isocyanoalkanoates - versatile synthons for the assembly of imidazoles |
| 856 | 4 | 0 | |u http://dx.doi.org/10.1002/(SICI)1522-2675(19990609)82:6<909::AID-HLCA909>3.0.CO;2-T |x Verlag |z kostenfrei registrierungspflichtig |3 Volltext |
| 856 | 4 | 0 | |u http://onlinelibrary.wiley.com/doi/10.1002/(SICI)1522-2675(19990609)82:6<909::AID-HLCA909>3.0.CO;2-T/abstract |x Verlag |z kostenfrei registrierungspflichtig |3 Volltext |
| 951 | |a AR | ||
| 992 | |a 20170428 | ||
| 993 | |a Article | ||
| 994 | |a 1999 | ||
| 998 | |g 1012574288 |a Neidlein, Richard |m 1012574288:Neidlein, Richard |d 140000 |e 140000PN1012574288 |k 0/140000/ |p 2 |y j | ||
| 998 | |g 1130894274 |a Bergemann, Marco |m 1130894274:Bergemann, Marco |d 170000 |d 170100 |d 160000 |d 160100 |e 170000PB1130894274 |e 170100PB1130894274 |e 160000PB1130894274 |e 160100PB1130894274 |k 0/170000/ |k 1/170000/170100/ |k 0/160000/ |k 1/160000/160100/ |p 1 |x j | ||
| 999 | |a KXP-PPN155767647X |e 2968163663 | ||
| BIB | |a Y | ||
| SER | |a journal | ||
| JSO | |a {"titleAlt":[{"title":"Studies on the reactivity of alpha-cyano-alpha-isocyanoalkanoates - versatile synthons for the assemby of imidazoles"}],"note":["Gesehen am 28.04.2017"],"type":{"media":"Online-Ressource","bibl":"article-journal"},"language":["eng"],"recId":"155767647X","title":[{"title_sort":"Studies on the reactivity of α-cyano-α-isocyanoalkanoates - versatile synthons for the assembly of imidazoles","title":"Studies on the reactivity of α-cyano-α-isocyanoalkanoates - versatile synthons for the assembly of imidazoles"}],"person":[{"role":"aut","display":"Bergemann, Marco","roleDisplay":"VerfasserIn","given":"Marco","family":"Bergemann"},{"family":"Neidlein","given":"Richard","roleDisplay":"VerfasserIn","display":"Neidlein, Richard","role":"aut"}],"physDesc":[{"extent":"9 S."}],"relHost":[{"physDesc":[{"extent":"Online-Ressource"}],"id":{"issn":["1522-2675"],"zdb":["1475013-2"],"doi":["10.1002/(ISSN)1522-2675"],"eki":["269534563"]},"origin":[{"publisherPlace":"New York, NY","dateIssuedKey":"1918","publisher":"Wiley-VCH","dateIssuedDisp":"1918-"}],"recId":"269534563","language":["ger","eng"],"note":["Gesehen am 15.05.2017","Fortsetzung der Druck-Ausgabe"],"type":{"media":"Online-Ressource","bibl":"periodical"},"disp":"Studies on the reactivity of α-cyano-α-isocyanoalkanoates - versatile synthons for the assembly of imidazolesHelvetica chimica acta","part":{"volume":"82","text":"82(1999), 6, Seite 909-918","extent":"9","year":"1999","pages":"909-918","issue":"6"},"pubHistory":["1.1918 -"],"title":[{"title":"Helvetica chimica acta","title_sort":"Helvetica chimica acta"}]}],"origin":[{"dateIssuedKey":"1999","dateIssuedDisp":"1999"}],"id":{"eki":["155767647X"],"doi":["10.1002/(SICI)1522-2675(19990609)82:6<909::AID-HLCA909>3.0.CO;2-T"]},"name":{"displayForm":["by Marco Bergemann and Richard Neidlein"]}} | ||
| SRT | |a BERGEMANNMSTUDIESONT1999 | ||