Reactions of 2,3-dihydrospiro[1H-4- and 5-azabenzimidazole-2,1′-cyclohexane] with nucleophiles: A potential route to some substituted aromatic heterocycles
The readily available title compounds 2, 16 and 27 react with pseudohalogenes (cyanide, azide), carbon and heterocyclic N-nucleophiles in the presence of manganese dioxide to give the corresponding substituted azaisobenzimidazoles (= 2H-azabenzimidazoles) 4, 8, 23-26 and 29-33, 36 or dihydroazabenzi...
Saved in:
| Main Authors: | , , |
|---|---|
| Format: | Article (Journal) |
| Language: | English |
| Published: |
1999
|
| In: |
Journal of heterocyclic chemistry
Year: 1999, Volume: 36, Issue: 1, Pages: 117-128 |
| ISSN: | 1943-5193 |
| DOI: | 10.1002/jhet.5570360118 |
| Online Access: | Verlag, kostenfrei registrierungspflichtig, Volltext: http://dx.doi.org/10.1002/jhet.5570360118 Verlag, kostenfrei registrierungspflichtig, Volltext: http://onlinelibrary.wiley.com/doi/10.1002/jhet.5570360118/abstract 
|
| Author Notes: | Ralf Reizner, Walter Kramer, and Richard Neidlein, Hans Suschitzky |
MARC
| LEADER | 00000caa a2200000 c 4500 | ||
|---|---|---|---|
| 001 | 1557673918 | ||
| 003 | DE-627 | ||
| 005 | 20230426153703.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 170428s1999 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1002/jhet.5570360118 |2 doi | |
| 035 | |a (DE-627)1557673918 | ||
| 035 | |a (DE-576)487673913 | ||
| 035 | |a (DE-599)BSZ487673913 | ||
| 035 | |a (OCoLC)1340969049 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rda | ||
| 041 | |a eng | ||
| 084 | |a 32 |2 sdnb | ||
| 100 | 1 | |a Reizner, Ralf |e VerfasserIn |0 (DE-588)1130892794 |0 (DE-627)885248449 |0 (DE-576)487673557 |4 aut | |
| 245 | 1 | 0 | |a Reactions of 2,3-dihydrospiro[1H-4- and 5-azabenzimidazole-2,1′-cyclohexane] with nucleophiles |b A potential route to some substituted aromatic heterocycles |c Ralf Reizner, Walter Kramer, and Richard Neidlein, Hans Suschitzky |
| 264 | 1 | |c 1999 | |
| 300 | |a 12 | ||
| 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 readily available title compounds 2, 16 and 27 react with pseudohalogenes (cyanide, azide), carbon and heterocyclic N-nucleophiles in the presence of manganese dioxide to give the corresponding substituted azaisobenzimidazoles (= 2H-azabenzimidazoles) 4, 8, 23-26 and 29-33, 36 or dihydroazabenzimidazoles (= 2,3-dihydro-1H-azabenzimidazoles 7, 22, 34 and 35. In 8 one of the two imidazolyl-substituents can be replaced by nucleophiles yielding the compounds 9-15. Treatment of 6′-bromo-2,3-dihydro-4-azabenzimidazole 16 with morpholine or piperidine results in loss of the Br-atom presumably by an AEa-mechanism. Reduction of the substituted azaisobenzimidazoles with sodium hydrosulfite followed by fission of the cyclohexane ring leads to substituted o-diaminopyridines. They were cyclised in situ with various condens ing agents to give new heterocyclic systems. Equimolar mixtures of some azaisobenzimidazoles and dihydroazabenzimidazoles lead to the formation of coloured charge transfer complexes stable only in the solid state. Owing to poor electron-acceptor properties the complex dissociates in solution. | ||
| 700 | 1 | |a Kramer, Walter |e VerfasserIn |0 (DE-588)1130892875 |0 (DE-627)885248600 |0 (DE-576)487673891 |4 aut | |
| 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 Journal of heterocyclic chemistry |d Hoboken, NJ [u.a.] : Wiley-Blackwell, 1964 |g 36(1999), 1, Seite 117-128 |h Online-Ressource |w (DE-627)326980105 |w (DE-600)2042274-X |w (DE-576)306829401 |x 1943-5193 |7 nnas |a Reactions of 2,3-dihydrospiro[1H-4- and 5-azabenzimidazole-2,1′-cyclohexane] with nucleophiles A potential route to some substituted aromatic heterocycles |
| 773 | 1 | 8 | |g volume:36 |g year:1999 |g number:1 |g pages:117-128 |g extent:12 |a Reactions of 2,3-dihydrospiro[1H-4- and 5-azabenzimidazole-2,1′-cyclohexane] with nucleophiles A potential route to some substituted aromatic heterocycles |
| 856 | 4 | 0 | |u http://dx.doi.org/10.1002/jhet.5570360118 |x Verlag |z kostenfrei registrierungspflichtig |3 Volltext |
| 856 | 4 | 0 | |u http://onlinelibrary.wiley.com/doi/10.1002/jhet.5570360118/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 3 | ||
| 998 | |g 1130892875 |a Kramer, Walter |m 1130892875:Kramer, Walter |d 170000 |d 170100 |d 160000 |d 160100 |e 170000PK1130892875 |e 170100PK1130892875 |e 160000PK1130892875 |e 160100PK1130892875 |k 0/170000/ |k 1/170000/170100/ |k 0/160000/ |k 1/160000/160100/ |p 2 | ||
| 998 | |g 1130892794 |a Reizner, Ralf |m 1130892794:Reizner, Ralf |d 170000 |d 170100 |d 160000 |d 160100 |e 170000PR1130892794 |e 170100PR1130892794 |e 160000PR1130892794 |e 160100PR1130892794 |k 0/170000/ |k 1/170000/170100/ |k 0/160000/ |k 1/160000/160100/ |p 1 |x j | ||
| 999 | |a KXP-PPN1557673918 |e 2968160478 | ||
| BIB | |a Y | ||
| SER | |a journal | ||
| JSO | |a {"title":[{"subtitle":"A potential route to some substituted aromatic heterocycles","title":"Reactions of 2,3-dihydrospiro[1H-4- and 5-azabenzimidazole-2,1′-cyclohexane] with nucleophiles","title_sort":"Reactions of 2,3-dihydrospiro[1H-4- and 5-azabenzimidazole-2,1′-cyclohexane] with nucleophiles"}],"person":[{"given":"Ralf","family":"Reizner","role":"aut","roleDisplay":"VerfasserIn","display":"Reizner, Ralf"},{"family":"Kramer","given":"Walter","roleDisplay":"VerfasserIn","display":"Kramer, Walter","role":"aut"},{"given":"Richard","family":"Neidlein","role":"aut","display":"Neidlein, Richard","roleDisplay":"VerfasserIn"}],"type":{"media":"Online-Ressource","bibl":"article-journal"},"note":["Gesehen am 28.04.2017"],"language":["eng"],"recId":"1557673918","origin":[{"dateIssuedDisp":"1999","dateIssuedKey":"1999"}],"id":{"eki":["1557673918"],"doi":["10.1002/jhet.5570360118"]},"name":{"displayForm":["Ralf Reizner, Walter Kramer, and Richard Neidlein, Hans Suschitzky"]},"physDesc":[{"extent":"12 S."}],"relHost":[{"physDesc":[{"extent":"Online-Ressource"}],"origin":[{"publisherPlace":"Hoboken, NJ [u.a.] ; Tampa, Fla.","dateIssuedDisp":"1964-","dateIssuedKey":"1964","publisher":"Wiley-Blackwell ; Hetero Corp."}],"id":{"issn":["1943-5193"],"zdb":["2042274-X"],"doi":["10.1002/(ISSN)1943-5193"],"eki":["326980105"]},"disp":"Reactions of 2,3-dihydrospiro[1H-4- and 5-azabenzimidazole-2,1′-cyclohexane] with nucleophiles A potential route to some substituted aromatic heterocyclesJournal of heterocyclic chemistry","type":{"bibl":"periodical","media":"Online-Ressource"},"note":["Gesehen am 27.01.15"],"recId":"326980105","language":["eng"],"pubHistory":["1.1964 -"],"part":{"extent":"12","text":"36(1999), 1, Seite 117-128","volume":"36","pages":"117-128","issue":"1","year":"1999"},"title":[{"title_sort":"Journal of heterocyclic chemistry","title":"Journal of heterocyclic chemistry"}]}]} | ||
| SRT | |a REIZNERRALREACTIONSO1999 | ||