ABSTRACTHeterocyclic compounds are widely distributed in nature and have played a vital role in synthetic organic chemistry. Five membered heterocycles, an important class of heterocyclic compounds, have been frequently synthesized and find a diverse range of applicatio More
ABSTRACTHeterocyclic compounds are widely distributed in nature and have played a vital role in synthetic organic chemistry. Five membered heterocycles, an important class of heterocyclic compounds, have been frequently synthesized and find a diverse range of applications in chemistry, biology and biochemistry of both pharmacological and chemical importance. Palladium-catalyzed cyclisation of different enynethiols has afforded a series of substituted thiophenes. The substrates, (Z)-2-en-4-yne-1- thiols, undergo cyclo isomerisation in dimethyl acetamide in the presence of catalytic amounts of PdI2 along with KI, to yield corresponding thiophenes 4 . Chiral imidazoles have been synthesized by thio-Ugi reaction . The method involves the treatment of thioamides with ammonia and cyclisation of the resulting substituted amidines in aqueous hydrochloric acid to afford corresponding imidazoles 11.This article will discuss on various synthetic pathways adopted for the synthesis of different five membered heterocycle derivatives and explore the mechanistic aspects apart from the recent applications of some unique compounds.
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The field of heterocyclic chemistry is vast and has played a significant role in synthetic organic chemistry. Heterocyclic compounds and methods for their synthesis form the bedrock of modern medicinal and pharmaceutical research. Indoles and Oxindoles are the most stud More
The field of heterocyclic chemistry is vast and has played a significant role in synthetic organic chemistry. Heterocyclic compounds and methods for their synthesis form the bedrock of modern medicinal and pharmaceutical research. Indoles and Oxindoles are the most studied bicyclic nitrogen heterocycles. The selective acylation of indoles often requires sensitive and reactive acyl chloride derivatives. A chemoselective N-acylation of indoles1 using thioesters 2 as a stable acyl source has been reported. Interaction of 1-acylindoles 10 with acetyl chloride in the presence of AlCl3 yields the corresponding 1- acyl-3-acetylindoles 11 which upon hydrolysis affords 3-acetylindole12.Addition of (1Hindol- 3-yl) magnesium iodide (16) to 2-(benzyloxy) acetyl chloride 17 in diethyl ether forms 3-benzyloxyacetylindole 18. Acylation of Oxindole 20 with chloroacetyl chloride affords 5- chloromethyl ketone derivatives31whichwhen treated with thioureas and thioamides leads to the formation of 5-thiazole oxindoles32.This article focuses on various synthetic methods and suggested mechanism of different indole and oxindole derivatives.Apart from this, applications of medicinal importance of these heteroatom compounds have also been discussed.
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