USE OF AZALACTONES IN A PICTET-SPENGLER-LIKE REACTION - STEREOSELECTIVE SYNTHESIS OF 1,3,4-SUBSTITUTED TETRAHYDRO-BETA-CARBOLINES

Authors
EZQUERRA J LAMAS C PASTOR A ALVAREZ P VAQUERO J PROWSE WG
Citation
J. Ezquerra et al., USE OF AZALACTONES IN A PICTET-SPENGLER-LIKE REACTION - STEREOSELECTIVE SYNTHESIS OF 1,3,4-SUBSTITUTED TETRAHYDRO-BETA-CARBOLINES, Tetrahedron letters, 37(32), 1996, pp. 5813-5816
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
32
Year of publication
1996
Pages
5813 - 5816
Database
ISI
SICI code
0040-4039(1996)37:32<5813:UOAIAP>2.0.ZU;2-2
Abstract
A ''Pictet-Spengler-like'' reaction between azalactones 1 and conforma tionally constrained tryptamines 4 in refluxing 1N HCl over 72 h. gave the corresponding tetrahydro-beta-carbolines 3 in moderate to good yi elds, The observed equatorial orientation of the C-1 substituent in th e THBC's results from a combination of the thermal reaction conditions and conformational constraints imposed by the starting tryptamines. C opyright (C) 1996 Elsevier Science Ltd