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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
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.
ISSN: 0040-4020
DOI: 10.1016/j.tet.2013.09.052
Rights: openAccess
Appears in Collections:FCTUC Química - Artigos em Revistas Internacionais

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