7 - Iranian Journal of Organic Chemistry Vol. 2, No. 1...

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Unformatted text preview: Iranian Journal of Organic Chemistry Vol. 2, No. 1 (2010) 310-313 S. Seyfi, I. Yavari 310 An effective synthesis of functionalized tetrahydro-4-oxoindeno[2,1- b ]pyrroles Samereh Seyfi * and Issa Yavari Chemistry Department, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran Abstract: A one-pot synthesis of dialkyl 1,3a,4,8b-tetrahydro-3a,8b-dihydroxy-1-alkyl-4-oxoindeno[1,2- b ]pyrrole-2,3- dicarboxylates via three-component reaction between indane-1,2,3-trione (ninhydrin), primary amines and dialkyl acetylenedicarboxylates is described. Keywords: Fused pyrroles; Three-component reaction; Benzylamine; Activated acetylenes. Introduction Five-membered, nitrogen-containing heterocycles are important building blocks in an extensive number of biologically active compounds [1]. Among them, pyrroles are heterocycles of great importance because of their presence in numerous natural products like heme, chlorophyll, vitamin B 12 , and various cytochrome enzymes [2]. Some of the recently isolated pyrrole-containing marine natural products have been found to exhibit considerable cytotoxicity and function as multidrug resistant reversal agents [3]. Many of these biologically active compounds have emerged as chemotherapeutic agents. In addition, polysubstituted pyrroles are molecular frameworks having immense importance in material science [4]. They have been also employed as antioxidants, antibacterial, ionotropic, antitumor, anti-inflammatory, and antifungal agents [5-10]. Moreover, they are a highly versatile class of intermediates in the synthesis of natural products as well as in heterocyclic chemistry [11]. Results and Discussion As part of our current studies on the development of new routes in heterocyclic synthesis,[12-14] we report an efficient procedure for direct synthesis of dihydroxy-tetrahydroindeno [2,1- b ] pyrrole -2,3- dicarboxylates ( 4 ) from the reaction of ninhydrin ( 1 ), acetylenic esters 2 and primary amines ( 3) at room temperature (Scheme 1). N O OH HO CO 2 R R' CO 2 R CO 2 R R'NH 2 + + O r.t., 5h O O CH 2 Cl 2 CO 2 R 85 87 90 75 84 Yield/ % 1 2 3 R' 4 a b c d e R Me Me Me Me Et Bn 4-Me-Bn 4-MeO-Bn 2-Cl-Bn Bn *Corresponding author. Tel: 09112267225; E-mail: seyfi_1363@yahoo.com Scheme 1 Iranian Journal of Organic Chemistry Vol. 2, No. 1 (2010) 310-313 S. Seyfi, I. Yavari 311 Structures of compounds 4a-e were assigned by IR, 1 H NMR, 13 C NMR and mass spectral data. The 1 H NMR spectrum of 4a exhibited four singlets for methoxy (3.55 and 3.78 ppm) and hydroxy (4.99 and 5.41 ppm) protons. Due to the presence of stereogenic centers in these products, the protons of CH 2 group are diasterotopic, and exhibit AB systems. The carbonyl groups resonances in the...
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7 - Iranian Journal of Organic Chemistry Vol. 2, No. 1...

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