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Vol. 26 No. 11 (2014): Vol 26 Issue 11

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Synthesis of 9,10-Substituted 3,4,10,10a-Tetrahydro-2H,9H-1-oxa-4a,9-diazaphenanthrenes by Reductive Cyclization Method

https://doi.org/10.14233/ajchem.2014.15859
V. Rajachandrasekhar
Ci Venti Chem (India) Private Limited, Plot No 72/A, Part 2 Phase-1, IDA Jeedimetla, Hyderabad-500 055, India
C. Hariprasad
Ci Venti Chem (India) Private Limited, Plot No 72/A, Part 2 Phase-1, IDA Jeedimetla, Hyderabad-500 055, India
V. Venugopala Rao
Ci Venti Chem (India) Private Limited, Plot No 72/A, Part 2 Phase-1, IDA Jeedimetla, Hyderabad-500 055, India
S. Venkataiah
Ci Venti Chem (India) Private Limited, Plot No 72/A, Part 2 Phase-1, IDA Jeedimetla, Hyderabad-500 055, India
P.K. Dubey
Department of Chemistry, Jawaharlal Nehru Technological University, Kukatpally, Hyderabad-500 085, India

Corresponding Author(s) : V. Rajachandrasekhar

shekar.valamoni@gmail.com

Asian Journal of Chemistry, Vol. 26 No. 11 (2014): Vol 26 Issue 11

Abstract

Commercially available o-phenylenediamine (1) was treated with methyl a-bromo-a-aryl acetate to obtain 3-aryl-3,4-dihydro-1H-quinoxalin-2-one (2). The latter was reacted with benzyl bromide to obtain 4-benzyl-3-aryl-3,4-dihydro-1H-quinoxalin-2-one (3). Treatment of 3 with ethyl 3-bromopropionate resulted in the formation of 3-(4-benzyl-3-aryl-2-oxo-3,4-dihydro-2H-quinoxalin-1-yl)propionic acid ethyl ester (4), which on reaction with LiAlH4 gave 9-benzyl-10-phenyl-3,4,10,10a-tetrahydro-2H,9H-1-oxa-4a,9-diazaphenanthrene (5) via a reductive cyclization. In another sequence of reactions, 2 was treated with benzyl chloroformate to obtain 3-oxo-2-aryl-3,4-dihydro-2H-quinoxalin-1-carboxylic acid benzyl esters (6). The latter on treatment with ethyl 3-bromopropionate gave 4-(2-ethoxycarbonylethyl)-3-oxo-2-phenyl- 3,4-dihydro-2H-quinoxaline-1-carboxylic acid benzyl esters (7). Then 7 was reductively cyclized with LiAlH4 to obtain 10-phenyl-3,4,10,10a-tetrahydro-2H-1-oxa-4a,9-diazaphenanthrene-9-carboxylic acid benzyl esters (8). In an yet another sequence of reactions, 2 was treated with catalytic amount of p-toluene sulphonic acid in toluene under refluxing conditions to obtain 3-phenyl-1H-quinoxaline-2-one (9). The latter, on treatment with ethyl 3-bromopropionate gave 3-[3-phenyl-2-oxo-2H-quinoxalin-1-yl]propionic acid ethyl esters (10), followed by reductive cyclization with LiAlH4 to afford 10-phenyl-3,4-dihydro-2H,10aH-1-oxa-4a,9-diazaphenanthrene (11). All the new products obtained in the above three sequences of reactions have been adequately characterized by spectral data.

Keywords

Synthesis Substituted diazaphenanthrenes Reductive cyclization
Rajachandrasekhar, V., Hariprasad, C., Venugopala Rao, V., Venkataiah, S., & Dubey, P. (2014). Synthesis of 9,10-Substituted 3,4,10,10a-Tetrahydro-2H,9H-1-oxa-4a,9-diazaphenanthrenes by Reductive Cyclization Method. Asian Journal of Chemistry, 26(11), 3161–3165. https://doi.org/10.14233/ajchem.2014.15859
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