Keteniminium Salts as Key Intermediates for the Efficient Synthesis of 3-Amino-Indoles and -Benzofurans
Helvetica Chimica Acta, cilt.103, sa.1, 2020 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 103 Sayı: 1
- Basım Tarihi: 2020
- Doi Numarası: 10.1002/hlca.201900217
- Dergi Adı: Helvetica Chimica Acta
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Agricultural & Environmental Science Database, Applied Science & Technology Source, Aquatic Science & Fisheries Abstracts (ASFA), Biotechnology Research Abstracts, CAB Abstracts, Chimica, Compendex, EMBASE, Veterinary Science Database, DIALNET
- Anahtar Kelimeler: aminobenzofuran, aminoindole, electrocyclic reactions, keteniminium
- Boğaziçi Üniversitesi Adresli: Evet
Özet
Herein, we describe a high yielding approach towards the synthesis of 3-amino-indoles and -benzofurans through 6π-electrocyclization. This was made possible by taking advantage of the high reactivity of keteniminium salts, formed in-situ by treating with triflic anhydride and 2-fluoropyridine amides bearing at the α-position either an aniline or a phenoxy moiety. These mild conditions, on top of furnishing rapidly the 3-aminobenzoheteroles, allow the tolerance of various functional groups. Control experiments were carried out to highlight that the keteniminium is, indeed, in most cases, the reactive intermediate and conformational preferences of such species were investigated through a DFT study.