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One-pot synthesis of polycyclic heterocyclic compounds by condensation of 1-carbamoylmethyl-2,3,3-trimethyl-3H-indolium salts with pyridine-2, 3, and 4- and quinoline-4-carboxaldehydes
Tetrahedron ( IF 2.1 ) Pub Date : 2018-05-15 , DOI: 10.1016/j.tet.2018.05.036
Algirdas Šačkus , Živilė Žukauskaitė , Neringa Kleizienė , Aurimas Bieliauskas , Virginė Amankavičienė , Wolfgang Holzer , Vytas Martynaitis

A one-pot synthesis of new polycyclic heterocyclic compounds was carried out via the condensation of 1-carbamoylmethyl-2,3,3-trimethyl-3H-indolium chloride with pyridine- and quinolinecarboxaldehydes. The heating of the aforementioned 3H-indolium salts with 1 eq. of pyridine-2, 3, and 4- or quinoline-4-carboxaldehyde in ethanol in the presence of piperidine as a catalyst provided 9a-[2-(pyridyl)ethenyl]- or 9a-[2-(quinolyl)ethenyl]-9,9a-dihydro-1H-imidazo[1,2-a]indol-2(3H)-one derivatives as the main products. However, reaction outcome was dramatically different for the analogous reactions in acetic acid. In this case, the heating of the chloride with 2 eq. of pyridine-2-carboxaldehyde afforded derivatives of 9a-[3-(pyridin-2-yl)indolizin-2-yl]-9,9a-dihydro-1H-imidazo[1,2-a]indol-2(3H)-one as the major product, while the use of 2 eq. of pyridine-3 and 4- or quinoline-4-carboxaldehyde led to the formation 2-heteroaryl-1-heteroarylmethyl-9H-pyrrolo[1,2-a]indole-3-carboxamides. Plausible pathways for the cyclization reactions are discussed. The structural assignments were based on 1H, 13C and 15N NMR spectroscopy, HRMS and single-crystal X-ray diffraction data.



中文翻译:

通过1-氨基甲酰基甲基-2,3,3-三甲基-3 H-吲哚鎓盐与吡啶-2、3和4-和喹啉-4-羧醛的缩合反应一锅合成多环杂环化合物

通过1-氨基甲酰基甲基-2,3,3-三甲基-3 H-吲哚鎓氯化物与吡啶-和喹啉甲醛的缩合反应,一锅合成新的多环杂环化合物。将上述3 H-吲哚盐以1当量加热。在哌啶为催化剂的条件下,在乙醇中对吡啶-2、3和4-或喹啉-4-甲醛进行反应,可得到9a- [2-(吡啶基)乙烯基]-或9a- [2-(喹啉基)乙烯基]- 9,9a-二氢-1 H-咪唑并[1,2- a ]吲哚-2(3 H)-衍生产品为主要产品。然而,对于乙酸中的类似反应,反应结果显着不同。在这种情况下,将氯化物加热至2当量。吡啶-2-甲醛的合成得到9a- [3-(吡啶-2-基)吲哚并嗪-2-基] -9,9a-二氢-1 H-咪唑并[1,2 - a ]吲哚-2(3 )的衍生物H)-一为主要产品,而使用2当量。吡啶-3和4-或喹啉-4-羧醛的合成导致形成2-杂芳基-1-杂芳基甲基-9 H-吡咯并[1,2- a ]吲哚-3-羧酰胺。讨论了环化反应的可能途径。结构分配基于1 H,13 C和15N NMR光谱,HRMS和单晶X射线衍射数据。

更新日期:2018-05-15
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