Cycloaddition and NH--Activation Strategies: Synthesis of Pyrazolopyrroloindoles, Imidazo-Pyridines, Tetrahydroisoquinolines and Benzimidazoquinazolines

Shinde, Anand Hari (2017) Cycloaddition and NH--Activation Strategies: Synthesis of Pyrazolopyrroloindoles, Imidazo-Pyridines, Tetrahydroisoquinolines and Benzimidazoquinazolines. PhD thesis, Indian Insitute of Technology Hyderabad.

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Abstract

Heterocyclic moieties are a prominent feature present in natural products, drug molecules and are known for their manifold properties, especially nitrogen heterocycles are of particular interest in medicinal chemistry, due to their diverse and important bi ological properties. Nature has displayed infinite diversity to incorporate these heterocyclic scaffolds into complex structures through evolution. Natural products confine to be the greatest inspiration in drug discovery. The structural complexity and div ersity of natural products, natural product inspired compound collections and the demand for developing efficient synthetic methods in a green and sustainable manner pose a daunting challenge to synthetic chemists. The creativity nature displays for hetero cyclic architecture is achieved by extensive use of cascade reactions in biosynthetic reactions. Inspired by this, more recently research has been focused on the development of cascade reaction sequences and multicomponent reactions in which multiple chemi cal transformation proceed consequently in one - pot fashion to generate molecular complexity. Cycloadditions combining atom economy, stereospecificity, stereoselectivity and the ability to generate molecular complexity in single step have been widely explor ed strategy in cascade transformations. Very recently CH/XH bond activations through catalytic sequential cascade have become one of the prime focuses of the synthetic chemists. H ybrid molecules embedded with different privileged scaffolds have long been attracted significantly due to their capability to enhance or modulate the biological properties of individual components. In this context, we were inspired to take up the challenge of developing novel sequential cascade transformation for the synthesis o f privileged heterocyclic scaffolds. Accordingly, we have developed novel cascade protocols for the synthesis of pyrazolopyrroloindoles, imidazopyridines, tetrahydroisoquinolines and benzimidazoquinazoline derivatives via cycloaddition reactions or metal catalyzed/mediated CH - activation strategies

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