Brønsted Acid Catalyzed (4 + 2) Cyclocondensation of 3-Substituted Indoles with Donor–Acceptor Cyclopropanes | Zendy

Alesandere Ortega | Zendy; Uxue Uria | Zendy; Tomás Tejero | Zendy; Liher Prieto | Zendy; Efraím Reyes | Zendy; Pedro Merino | Zendy; José L. Vicário | Zendy

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Brønsted Acid Catalyzed (4 + 2) Cyclocondensation of 3-Substituted Indoles with Donor–Acceptor Cyclopropanes

Author(s) -

Alesandere Ortega,

Uxue Uria,

Tomás Tejero,

Liher Prieto,

Efraím Reyes,

Pedro Merino,

José L. Vicário

Publication year - 2021

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.1c00470

Subject(s) - chemistry , catalysis , brønsted–lowry acid–base theory , acceptor , combinatorial chemistry , organic chemistry , medicinal chemistry , stereochemistry , physics , condensed matter physics

Acylcyclopropanes are employed as useful donor-acceptor cyclopropanes that undergo formal (4 + 2) cyclocondensation with N -unprotected 3-substituted indoles in the presence of a Brønsted acid catalyst. The reaction involves the simultaneous alkylation of both the N and C-2 positions of the indole and provides access to the 8,9-dihydropyrido[1,2- a ]indole scaffold that is the central core of several biologically relevant indole alkaloids in excellent yields and good selectivities.

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