TY - JOUR
T1 - Study of the reaction between carbamoyl azides of α-N-protected amino acids and hydrazine monohydrate
AU - Verardo, Giancarlo
AU - Venneri, Cesare Daniele
AU - Esposito, Gennaro
AU - Strazzolini, Paolo
PY - 2011/3
Y1 - 2011/3
N2 - Two simple and efficient synthetic methods for the preparation of semicarbazide amino acid derivatives are reported. The procedures involve reaction between the carbamoyl azides of α-N-protected amino acids and hydrazine monohydrate: 4-[(alkoxycarbonylamino)(alkyl)methyl]semicarbazides 1 are obtained when hydrazine is added to the separated tetrahydrofuran (THF) solution containing the carbamoyl azide at 0 °C, whereas 1-[(alkoxycarbonylamino)(alkyl)methyl-carbamoyl]-4-[(alkoxycarbonylamino)(alkyl) methyl]semicarbazides 4 are produced by adding hydrazine directly into the final THF/aqueous buffer (KH2PO4) biphasic mixture containing the prepared carbamoyl azide at 50 °C, respectively. NMR experimental data obtained from samples dissolved in [D6]dimethyl sulfoxide suggest a dimeric association for semicarbazides 4 with intermolecular hydrogen bonds. Moreover, the ESI-MS-MS spectra reveal some interesting common features.
AB - Two simple and efficient synthetic methods for the preparation of semicarbazide amino acid derivatives are reported. The procedures involve reaction between the carbamoyl azides of α-N-protected amino acids and hydrazine monohydrate: 4-[(alkoxycarbonylamino)(alkyl)methyl]semicarbazides 1 are obtained when hydrazine is added to the separated tetrahydrofuran (THF) solution containing the carbamoyl azide at 0 °C, whereas 1-[(alkoxycarbonylamino)(alkyl)methyl-carbamoyl]-4-[(alkoxycarbonylamino)(alkyl) methyl]semicarbazides 4 are produced by adding hydrazine directly into the final THF/aqueous buffer (KH2PO4) biphasic mixture containing the prepared carbamoyl azide at 50 °C, respectively. NMR experimental data obtained from samples dissolved in [D6]dimethyl sulfoxide suggest a dimeric association for semicarbazides 4 with intermolecular hydrogen bonds. Moreover, the ESI-MS-MS spectra reveal some interesting common features.
KW - Amino acids
KW - Azides
KW - Semicarbazides
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U2 - 10.1002/ejoc.201001385
DO - 10.1002/ejoc.201001385
M3 - Article
AN - SCOPUS:79951804258
SN - 1434-193X
SP - 1376
EP - 1384
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
IS - 7
ER -