Straightforward Synthesis of 3-Aminothiophenes Using Activated Amides
Helvetica Chimica Acta, cilt.102, sa.4, 2019 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 102 Sayı: 4
- Basım Tarihi: 2019
- Doi Numarası: 10.1002/hlca.201900031
- Dergi Adı: Helvetica Chimica Acta
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Anahtar Kelimeler: amide activation, aminothiophenes, electrocyclic reactions, keteniminium salts
- Boğaziçi Üniversitesi Adresli: Evet
Özet
Herein, we describe a facile approach towards the synthesis of diversely substituted 3-aminothiophenes. A wide range of functional groups can be incorporated at the C(2), C(4), and C(5) positions of the thiophenes, and this route is also suitable for the synthesis of fused bicyclic heterocycles such as 3-aminotetrahydrobenzothiophenes. This methodology relies on a 6π-electrocyclization involving a vinyl sulfide linked to a keteniminium salt, the latter being formed in-situ through activation of the corresponding amide with triflic anhydride.