Guin Soumitra, Gupta Raman, Majee Debashis, Samanta Sampak
Discipline of Chemistry, Indian Institute of Technology Indore, Simrol, Indore, 453552, Madhya Pradesh, India.
Beilstein J Org Chem. 2018 Nov 2;14:2771-2778. doi: 10.3762/bjoc.14.254. eCollection 2018.
An intriguing DABCO-catalyzed and DBU-promoted one-pot synthesis of an important class of (2-hydroxyaryl)pyridine derivatives bearing a carboxylate or a nitrile group suitably placed at C3 position of the aza-ring has been achieved in acceptable chemical yields with a broad functional group tolerance. This sequential C-C/C-N bond making process proceeds through a regioselective allylic alkylation/aza-Michael reaction between MBH carbonates derived from an acrylate/acrylonitrile and -sulfonyl ketimines as C,N-binucleophiles catalyzed by DABCO, followed by elimination of SO under the influence of base and subsequent aromatization in an open atmosphere.
实现了一种有趣的由1,4-二氮杂双环[2.2.2]辛烷（DABCO）催化、1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）促进的一锅法合成一类重要的（2-羟基芳基）吡啶衍生物，这类衍生物在氮杂环的C3位上合适地带有羧酸酯或腈基，反应以可接受的化学产率进行，并且对官能团具有广泛的耐受性。这种顺序的C-C/C-N键形成过程通过由DABCO催化的丙烯酸酯/丙烯腈衍生的MBH碳酸酯与作为C,N-双亲核试剂的磺酰基酮亚胺之间的区域选择性烯丙基烷基化/氮杂-Michael反应进行，随后在碱的影响下消除SO，并在开放气氛中进行后续的芳构化。
