Sequential amination/annulation/aromatization reaction of carbonyl compounds and propargylamine: A new one-pot approach to functionalized pyridines
Sequential amination/annulation/aromatization reaction of carbonyl compounds and propargylamine: A new one-pot approach to functionalized pyridines
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DOI：
10.1021/jo0347260
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发表时间：
2003-09-05
影响因子：
3.6
通讯作者：
Rossi, E
中科院分区：
文献类型：
--
作者：
Abbiati, G;Arcadi, A;Rossi, E
以二烷基无环/环酮1a- 1、甲基、芳基/杂芳基酮1m- 1、含α -氢的醛1s，t与丙胺2为原料，用一锅法合成吡啶4a-t。金盐和铜盐是酮与2反应的有效催化剂。吡啶4的形成被认为是通过羰基化合物的顺序胺化，然后是n -丙炔胺（n -丙炔二胺）中间体3(5)的区域选择性6-内环化和芳构化反应。线性多环吡啶4i可由胆甾-3- 1 - 1i与2反应制备，而角型多环吡啶4j则由胆甾-5-en-3- 1 - 1j开始制备。研究了多环二羰基1k， 1与2反应的选择性。
A general one-pot synthesis of pyridines 4a-t from the reaction of dialkyl acyclic/cyclic ketones 1a-i, methyl, aryl/heteroaryl ketones 1m-r, and aldehydes bearing alpha-hydrogens 1s,t with propargylamine 2 is described. Gold and copper salts are efficient catalysts for the reaction of ketones with 2. The formation of the pyridines 4 is suggested to proceed through the sequential amination of carbonyl compounds followed by regioselective 6-endo-dig cyclization of the N-propargylenamine (N-propargyldienamine) intermediate 3(5) and aromatization reaction. Whereas the preparation of linear polycyclic pyridine 4i can be carried out by reacting cholestan-3-one 1i with 2, the angular polycyclic pyridine 4j has been obtained starting from cholest-5-en-3-one 1j. Selectivity of the reaction of polycyclic dicarbonyls 1k,l with 2 has also been investigated.