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Synlett 2007(3): 0480-0484  
DOI: 10.1055/s-2007-967999
LETTER
© Georg Thieme Verlag Stuttgart · New York

A Facile and Efficient Synthesis of New Polysubstituted Indeno[1,2-b]pyri­dines via One-Pot, Three-Component Microwave-Assisted Reaction

Shujiang Tu*, Bo Jiang, Junyong Zhang, Yan Zhang, Runhong Jia, Chunmei Li, Dianxiang Zhou, Longji Cao, Qingqing Shao
Department of Chemistry, Xuzhou Normal University, Key Laboratory of Biotechnology for Medicinal Plant, Xuzhou, Jiangsu 221116, P. R. of China
Fax: +86(516)83403164; e-Mail: laotu@xznu.edu.cn;
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Publication History

Received 16 September 2006
Publication Date:
07 February 2007 (online)

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Abstract

A rapid and efficient method is developed to synthesize new polysubstituted indeno[1,2-b]pyridines via three-component microwave-assisted reaction of arylidenemalononitrile, 1,3-indane­dione and aromatic amine. This method has the advantages of short synthetic route, operational simplicity, increased safety for small-scale high-speed synthesis, and minimal environmental impact.

Key words

arylidenemalononitrile - indenopyridine derivatives - multicomponent - heterocycles - amines

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Typical Procedure: Preparation of Compounds 5, 7 and 10.
The reactions were performed in a monomodal EmrysTM Creator from Personal Chemistry, Uppsala, Sweden. In an EmrysTM reaction vial (10 mL), arylidenemalononitrile (2, 1 mmol), 1,3-indenodione (3, 1 mmol) or dimedone (8, 1 mmol), aromatic amine (4, 1.2 mmol) or aliphatic amine (6, 1.2 mmol) and DMF (1.0 mL) were mixed and then capped. The mixture was irradiated for 4-9 min at 120 °C under microwave irradiation (initial power 100 W and maximum power 200 W). Upon completion of the reaction as monitored by TLC, the reaction mixture was cooled to r.t. and then poured into cold H2O. The solid product was filtered, washed with H2O and EtOH (95%). The solid was purified by recrystallization from EtOH (95%). Spectral data and elemental analyses of selected compounds are given here.
Compound 5g: IR (KBr): ν = 3301, 2208, 1711, 1606, 1559, 1497, 1387, 1329, 753, 704 cm-1. 1H NMR (DMSO-d 6): δ = 9.92 (s, 1 H, NH), 7.95 (d, 1 H, J = 4.8 Hz, thiophenyl-H), 7.71 (t, 4 H, J = 7.6 Hz, ArH), 7.65-7.58 (m, 3 H, ArH), 7.44 (t, 2 H, J = 8.0 Hz, ArH), 7.29 (t, 1 H, J = 4.4 Hz, thiophenyl-H), 7.23-7.20 (m, 1 H, thiophenyl-H) ppm. Anal. Calcd for C23H13N3OS: C, 72.80; H, 3.45; N, 11.07; S, 8.45. Found: C, 72.97; H, 3.34; N, 11.21; S, 8.34.
Compound 5k: IR (KBr): ν = 3306, 2213, 1713, 1610, 1571, 1520, 1240, 1009, 813, 763 cm-1. 1H NMR (DMSO-d 6): δ = 9.90 (s, 1 H, NH), 7.76 (d, 2 H, J = 8.4 Hz, ArH), 7.70-7.68 (m, 2 H, ArH), 7.61-7.60 (m, 2 H, ArH), 7.58 (d, 2 H, J = 8.4 Hz, ArH), 7.53 (d, 2 H, J = 8.4 Hz, ArH), 7.24 (d, 2 H, J = 8.4 Hz, ArH), 2.35 (s, 3 H, CH3) ppm. Anal. Calcd for C26H16BrN3O: C, 66.97; H, 3.46; N, 9.01. Found: C, 66.89; H, 3.54; N, 9.17.
Compound 7a: IR (KBr): ν = 3437, 3335, 2218, 1702, 1621, 1572, 1355, 1201, 1007, 749; 656 cm-1. 1H NMR (DMSO-d 6): δ = 7.74 (d, 2 H, J = 8.4 Hz, ArH), 7.67-7.65 (m, 2 H, ArH), 7.58-7.56 (m, 2 H, ArH), 7.57 (d, 2 H, J = 8.4 Hz, ArH), 5.46 (s, 2 H, NH2), 4.98 (s, 1 H, CH) ppm. Anal. Calcd for C19H11BrN2O2: C, 60.18; H, 2.92; N, 7.39. Found: C, 60.35; H, 2.74; N, 7.25.