Unprecedented nucleophile-promoted 1,7-S or Se shift reactions under Pummerer reaction conditions of 4-alkenyl-3-sulfinylmethylpyrroles
A unique 1,7-S- and Se-shift reaction under Pummerer reaction conditions of 4-alkenyl-3-sulfinyl- and seleninylpyrroles was described. The usual Pummerer reaction of 4-(alkenylaminomethyl)-3-phenylsulfinylpyrroles and a successive reaction with tetrabutylammonium hydroxide (TBAH) yielded either pyrr...
| Main Authors: | , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2018-10-01
|
| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.14.250 |
| id |
doaj-77a754f866274044ad5e9894d9a2a3a8 |
|---|---|
| record_format |
Article |
| spelling |
doaj-77a754f866274044ad5e9894d9a2a3a82021-02-02T00:48:14ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972018-10-011412722272910.3762/bjoc.14.2501860-5397-14-250Unprecedented nucleophile-promoted 1,7-S or Se shift reactions under Pummerer reaction conditions of 4-alkenyl-3-sulfinylmethylpyrrolesTakashi Go0Akane Morimatsu1Hiroaki Wasada2Genzoh Tanabe3Osamu Muraoka4Yoshiharu Sawada5Mitsuhiro Yoshimatsu6Department of Chemistry, Faculty of Education, Gifu University, Yanagido 1-1, Gifu 501-1193, JapanDepartment of Chemistry, Faculty of Education, Gifu University, Yanagido 1-1, Gifu 501-1193, JapanDepartment of Chemistry, Faculty of Regional Study, Gifu University, Yanagido 1-1, Gifu 501-1193, JapanSchool of Pharmacy, Kindai University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, JapanSchool of Pharmacy, Kindai University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, JapanLife Science Research Center, Gifu University, Yanagido 1-1, Gifu 501-1193, JapanDepartment of Chemistry, Faculty of Education, Gifu University, Yanagido 1-1, Gifu 501-1193, JapanA unique 1,7-S- and Se-shift reaction under Pummerer reaction conditions of 4-alkenyl-3-sulfinyl- and seleninylpyrroles was described. The usual Pummerer reaction of 4-(alkenylaminomethyl)-3-phenylsulfinylpyrroles and a successive reaction with tetrabutylammonium hydroxide (TBAH) yielded either pyrrolo[3,2-c]azepines or N-pyrrol-3-ylmethyl-N-(4-hydroxy-3-sulfanylpropyl)-p-toluenesulfonamides (diols). Seleno-Pummerer reactions of 3-selanylmethylpyrroles also proceeded via in situ generation of selenoxides, followed by a treatment with TBAH.https://doi.org/10.3762/bjoc.14.250hydroaminationPummerer reactionpyrrolepyrroloazepine1,7-sulfur shift |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Takashi Go Akane Morimatsu Hiroaki Wasada Genzoh Tanabe Osamu Muraoka Yoshiharu Sawada Mitsuhiro Yoshimatsu |
| spellingShingle |
Takashi Go Akane Morimatsu Hiroaki Wasada Genzoh Tanabe Osamu Muraoka Yoshiharu Sawada Mitsuhiro Yoshimatsu Unprecedented nucleophile-promoted 1,7-S or Se shift reactions under Pummerer reaction conditions of 4-alkenyl-3-sulfinylmethylpyrroles Beilstein Journal of Organic Chemistry hydroamination Pummerer reaction pyrrole pyrroloazepine 1,7-sulfur shift |
| author_facet |
Takashi Go Akane Morimatsu Hiroaki Wasada Genzoh Tanabe Osamu Muraoka Yoshiharu Sawada Mitsuhiro Yoshimatsu |
| author_sort |
Takashi Go |
| title |
Unprecedented nucleophile-promoted 1,7-S or Se shift reactions under Pummerer reaction conditions of 4-alkenyl-3-sulfinylmethylpyrroles |
| title_short |
Unprecedented nucleophile-promoted 1,7-S or Se shift reactions under Pummerer reaction conditions of 4-alkenyl-3-sulfinylmethylpyrroles |
| title_full |
Unprecedented nucleophile-promoted 1,7-S or Se shift reactions under Pummerer reaction conditions of 4-alkenyl-3-sulfinylmethylpyrroles |
| title_fullStr |
Unprecedented nucleophile-promoted 1,7-S or Se shift reactions under Pummerer reaction conditions of 4-alkenyl-3-sulfinylmethylpyrroles |
| title_full_unstemmed |
Unprecedented nucleophile-promoted 1,7-S or Se shift reactions under Pummerer reaction conditions of 4-alkenyl-3-sulfinylmethylpyrroles |
| title_sort |
unprecedented nucleophile-promoted 1,7-s or se shift reactions under pummerer reaction conditions of 4-alkenyl-3-sulfinylmethylpyrroles |
| publisher |
Beilstein-Institut |
| series |
Beilstein Journal of Organic Chemistry |
| issn |
1860-5397 |
| publishDate |
2018-10-01 |
| description |
A unique 1,7-S- and Se-shift reaction under Pummerer reaction conditions of 4-alkenyl-3-sulfinyl- and seleninylpyrroles was described. The usual Pummerer reaction of 4-(alkenylaminomethyl)-3-phenylsulfinylpyrroles and a successive reaction with tetrabutylammonium hydroxide (TBAH) yielded either pyrrolo[3,2-c]azepines or N-pyrrol-3-ylmethyl-N-(4-hydroxy-3-sulfanylpropyl)-p-toluenesulfonamides (diols). Seleno-Pummerer reactions of 3-selanylmethylpyrroles also proceeded via in situ generation of selenoxides, followed by a treatment with TBAH. |
| topic |
hydroamination Pummerer reaction pyrrole pyrroloazepine 1,7-sulfur shift |
| url |
https://doi.org/10.3762/bjoc.14.250 |
| work_keys_str_mv |
AT takashigo unprecedentednucleophilepromoted17sorseshiftreactionsunderpummererreactionconditionsof4alkenyl3sulfinylmethylpyrroles AT akanemorimatsu unprecedentednucleophilepromoted17sorseshiftreactionsunderpummererreactionconditionsof4alkenyl3sulfinylmethylpyrroles AT hiroakiwasada unprecedentednucleophilepromoted17sorseshiftreactionsunderpummererreactionconditionsof4alkenyl3sulfinylmethylpyrroles AT genzohtanabe unprecedentednucleophilepromoted17sorseshiftreactionsunderpummererreactionconditionsof4alkenyl3sulfinylmethylpyrroles AT osamumuraoka unprecedentednucleophilepromoted17sorseshiftreactionsunderpummererreactionconditionsof4alkenyl3sulfinylmethylpyrroles AT yoshiharusawada unprecedentednucleophilepromoted17sorseshiftreactionsunderpummererreactionconditionsof4alkenyl3sulfinylmethylpyrroles AT mitsuhiroyoshimatsu unprecedentednucleophilepromoted17sorseshiftreactionsunderpummererreactionconditionsof4alkenyl3sulfinylmethylpyrroles |
| _version_ |
1724313057513963520 |