Pyrazine chemistry. Part 11. Chemical studies on cyclic tautomers of cyclo-L-propyl-L-tryptophyl and its derivatives
- 1 January 1979
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 12,p. 3048-3052
- https://doi.org/10.1039/p19790003048
Abstract
Simple derivatives of tryptophan, including cyclo-L-propyl-L-tryptophyl, can form cyclic tautomers involving formation of the hexahydropyrrolo[2,3-b]indole system (6) by treatment with strong protic or Lewis acids. The cyclic tautomers are useful in synthetic transformations since selective acylation or alkylation of the indolic nitrogen atoms is possible. In this manner a 3,3-dimethylallyl substituent can be introduced into the indolic nitrogen of the title compound to produce (1). The N-substituted derivatives readily open up, under acid catalysis, to regenerate the N-substituted indole system (3).This publication has 3 references indexed in Scilit:
- Pyrazine chemistry. Part 10. Synthesis of alkylated derivatives of piperazine-2,5-dionesJournal of the Chemical Society, Perkin Transactions 1, 1979
- Cyclic peptides. 14. Conformational energy and circular dichroism of proline-containing cyclic dipeptidesJournal of the American Chemical Society, 1976
- Electrophilic substitution in indoles—ITetrahedron, 1965