A three-component domino protocol for the facile synthesis of highly functionalized tetrahydroisoquinolines by creation of their benzene ring

6-Amino-2-methyl-8-phenyl-1,2,3,4-tetrahydroisoquinoline-5,7-dicarbonitrile

“…The development of efficient synthetic methods for isoquinoline and related derivatives is continuously attracting the attention of many chemists (Rong et al, 2010;Balamurugan et al, 2011). As a part of our current studies on the development of new routes in organic synthesis and the screen of anticancer drugs, in this article, we report the crystal structure of the title compound (Fig.…”

“…For background to natural products containing an isoquinoline backbone, see: Marchand et al (2006); Cho et al (2007); Van Quaquebeke et al (2007). For related structures, see: Rong et al (2010); Balamurugan et al (2011). Table 1 Hydrogen-bond geometry (Å , ).…”

Stereocontrolled Synthesis of Functionalized Azaheterocycles from Carbocycles through Oxidative Ring Opening/Reductive Ring Closing Protocols

“…The route, starting from a protected cyclohexenetriol, included only three steps: ozonolysis, reductive amination, and deprotection (Scheme 12). [72,73] Robinson et al developed an effective synthesis of a series of novel analogs of the antibacterial agent gemmacin B with a bridged azepane framework (81). The key steps are oxidative ring opening/ring closing through reductive amination (Scheme 13).…”

“…[74][75][76][77][78][79] Because of these relevant properties, many synthetic approaches towards the creation of an isoquinoline or THIQ core have been described so far. [80][81][82][83][84][85][86][87] The well-known procedures are the Pictet-Spengler, Bischer-Napieralski, and Pomeranz-Fritsch-Bobbit cyclizations, which are widely-applied synthetic methodologies to create a number of important isoquinoline alkaloids. [80] Fluorine-containing tetrahydroisoquinoline or isoquinoline derivatives constitute an important area of fluorinated molecules either as pharmaceuticals or agrochemicals.…”

Stereocontrolled synthesis of functionalized fluorine-containing N-heterocycles through oxidative ring opening/ring closure with reductive amination

“…Several drugs, such as some antidiuretics, antidepressants, hallucinogens and antihypertensive agents, contain a THIQ motif 33,[93][94][95][96][97][98] . Because of these important properties, a large number of synthetic approaches towards the creation of an isoquinoline or THIQ core have been described so far 95,[99][100][101][102][103][104][105][106] . The best-known procedures are the Pictet-Spengler, Bischer-Napieralski, and…”