Concise Synthesis of Annulated Pyrido[3,4-b]indoles via Rh(I)-Catalyzed Cyclization.

Autor: Varelas JG; Department of Chemistry and Biochemistry, Providence College , 1 Cunningham Square, Providence, Rhode Island 02918, United States., Khanal S; Department of Chemistry and Biochemistry, Providence College , 1 Cunningham Square, Providence, Rhode Island 02918, United States., O'Donnell MA; Department of Chemistry and Biochemistry, Providence College , 1 Cunningham Square, Providence, Rhode Island 02918, United States., Mulcahy SP; Department of Chemistry and Biochemistry, Providence College , 1 Cunningham Square, Providence, Rhode Island 02918, United States.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2015 Nov 06; Vol. 17 (21), pp. 5512-4. Date of Electronic Publication: 2015 Oct 23.
DOI: 10.1021/acs.orglett.5b02807
Abstrakt: The synthesis of pyridines bearing multiple ring fusions poses a considerable challenge for organic chemists. To address this problem, we describe the synthesis of a small library of pyrido[3,4-b]indoles via an efficient, five-step sequence. The key transformation is a Rh(I)-catalyzed [2 + 2 + 2] cyclization that forms three rings in one reaction flask. Our method is high yielding, accommodates a variety of functional groups, and suffers no entropic costs as ring size increases.
Databáze: MEDLINE