Studies on Mechanism of Formation and Medicinal applications of structurally diverse Indole and Oxindole derivatives
محورهای موضوعی : Organic and Inorganic synthesis
Noor ud Din Zargar
1
(University of Kashmir J& K)
Khaliq Zaman Khan
2
(Department of Chemistry University Of Kashmir Srinagar (190006) J&K India)
کلید واژه: Acylation, Indole, Oxindole, Heterocycles, Synthesis, Mechanism,
چکیده مقاله :
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.
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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