Please use this identifier to cite or link to this item:
https://hdl.handle.net/10316/27452
Title: | Reactivity of sarcosine and 1,3-thiazolidine-4-carboxylic acid towards salicylaldehyde-derived alkynes and allenes | Authors: | Laia, Fernanda M. Ribeiro Gomes, Clara S. B. Melo, Teresa M. V. D. Pinho e |
Keywords: | Cycloaddition; Azomethine ylides; Chromeno[4,3-b]pyrroles; Chromeno-pyrrolo[1,2-c]thiazoles; Chromeno[2,3-b]pyrrole; Pyrroles; Allenes; Sarcosine; Thiazolidine | Issue Date: | 25-Nov-2013 | Publisher: | Elsevier | Citation: | LAIA, Fernanda M. Ribeiro; GOMES, Clara S. B.; MELO, Teresa M. V. D. Pinho e - Reactivity of sarcosine and 1,3-thiazolidine-4-carboxylic acid towards salicylaldehyde-derived alkynes and allenes. "Tetrahedron". ISSN 0040-4020. Vol. 69 Nº. 47 (2013) p. 10081-10090 | Serial title, monograph or event: | Tetrahedron | Volume: | 69 | Issue: | 47 | Abstract: | The reaction of sarcosine and 1,3-thiazolidine-4-carboxylic acid with salicylaldehyde-derived alkynes and allenes opened the way to new chromeno[4,3-b]pyrrole and chromeno[2,3-b]pyrrole derivatives. Tetrahydro-chromeno[4,3-b]pyrroles were obtained from the reaction of these secondary amino acids with O-propargylsalicylaldehyde. Interestingly, sarcosine reacted with ethyl 4-(2-formylphenoxy)but-2-ynoate to give a monocyclic pyrrole resulting from rearrangement of the initially formed 1,3-dipolar cycloadduct. Decarboxylative condensation of ethyl 4-(2-formylphenoxy)but-2-ynoate with 1,3-thiazolidine-4-carboxylic acid afforded in a stereoselective fashion the expected chromeno-pyrrolo[1,2-c]thiazole, which structure was unambiguously established by X-ray crystallography. However, the 1H,3H-pyrrolo[1,2-c]thiazole resulting from the opening of the pyran ring was also isolated. The reaction with O-buta-2,3-dienyl salicylaldehyde afforded 3-methylene-hexahydrochromeno[4,3-b]pyrrole. O-Allenyl salicylaldehyde reacted with sarcosine and 1,3-thiazolidine-4-carboxylic acid to give a new type of chromeno-pyrroles. A mechanism proposal for the synthesis of these chromeno[2,3-b]pyrroles has been presented. | URI: | https://hdl.handle.net/10316/27452 | ISSN: | 0040-4020 | DOI: | 10.1016/j.tet.2013.09.052 | Rights: | openAccess |
Appears in Collections: | FCTUC Química - Artigos em Revistas Internacionais |
Files in This Item:
File | Description | Size | Format | |
---|---|---|---|---|
Reactivity of Sarcosine and 1,3-Thiazolidine-4-carboxylic Acid.pdf | 1.51 MB | Adobe PDF | View/Open |
SCOPUSTM
Citations
10
checked on Nov 9, 2022
WEB OF SCIENCETM
Citations
5
10
checked on Jul 2, 2022
Page view(s)
304
checked on Sep 24, 2024
Download(s)
312
checked on Sep 24, 2024
Google ScholarTM
Check
Altmetric
Altmetric
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.