N-(1-Acylaminoalkyl)amidinium salts derived from DBU or related bases as reactive intermediates in alpha-amidoalkylation reactions

作者：Pazdzierniok Holewa Agnieszka; Adamek Jakub; Zielinska Katarzyna; Piernikarczyk Katarzyna; Mazurkiewicz Roman^*

来源：ARKIVOC, 2012, 314-329.

• 1-(N-Acylamino)alkyltriphenylphosphonium salts
• 1-(N-acylamino)alkylamidinium salts
• alpha-amidoalkylation
• N-acylimines
• enamides
• non-nucleophilic bases

1-(N-Acylamino)alkyltriphenylphosphonium salts 4, when treated with DBU, DBN or TBD in CD3CN or MeCN, were transformed immediately into the corresponding 1-(N-acylamino)alkylamidinium or guanidinium salts 5. Salts 5 with a proton at the a-position underwent slow transformation to the corresponding enamides 6. 1-(N-Acylamino)alkyltriphenylphosphonium salts 4, amidinium or guanidinium salts 5, as well as enamides 6 reacted readily with beta-dicarbonyl compounds in the presence of corresponding base under microwave irradiation at 60 degrees C to give the expected product of alpha-amidoalkylation of the enolate anion. The role of 1-(N-acylamino) alkylamidinium or guanidinium salts 5 as reactive intermediates in alpha-amidoalkylation with 1-(N-acylamino) alkyltriphenylphosphonium salts is discussed.

• 出版日期2012