Cycloaddition of dimethyl acetylenedicarboxylate to indoles. Isolation of a [2 + 2] adduct | Zendy

Augusto J. | Zendy; Rodriguez R. | Zendy; Verardo L. I. | Zendy

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Cycloaddition of dimethyl acetylenedicarboxylate to indoles. Isolation of a [2 + 2] adduct

Author(s) -

Augusto J.,

Rodriguez R.,

Verardo L. I.

Publication year - 1983

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570200523

Subject(s) - dimethyl acetylenedicarboxylate , chemistry , boron trifluoride , adduct , cycloaddition , solvent , medicinal chemistry , organic chemistry , catalysis , cyclobutene , ring (chemistry)

Thermal reaction of 1,2,3‐trimethylindole (1) and 1,3‐dimethylindole (5) with dimethyl acetylenedicarboxylate in the presence of boron trifluoride etherate gave cyclobutene derivatives 2 and 7 that were isolated for the first time in good yields under themal conditions. In a polar solvent and with an excess of catalyst, 4‐methoxy‐2,4a‐dihydro‐4a,9‐dimethyl‐2‐oxacarbazole 4 was obtained in yields up to 72%.

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