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Synthesis 2006(22): 3874-3882  
DOI: 10.1055/s-2006-950297
PAPER
© Georg Thieme Verlag Stuttgart · New York

One-Pot Synthesis of N-Substituted Azapodophyllotoxin Derivatives under Microwave Irradiation

Shujiang Tu*a, Yan Zhanga, Bo Jianga, Runhong Jiaa, Junyong Zhanga, Jinpeng Zhangb, Shunjun Ji*b
a 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;
b College of Chemistry and Chemical Engineering, Key Laboratory of Organic Synthesis of Jiangsu Province, Suzhou University, Suzhou, P. R. of China
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Publication History

Received 14 June 2006
Publication Date:
09 October 2006 (online)

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Abstract

A series of new, N-substituted azapodophyllotoxin derivatives were synthesized via a three-component reaction of an aldehyde, an enaminone and tetronic acid in glacial acetic acid, under microwave irradiation, without a catalyst. This new protocol has the advantages of shorter time, higher yields, lower cost and broader substrate scope, as well as easier operation.

Key words

microwave irradiation - tetronic acid - enaminone - N-substituted furo[3,4-b]quinoline - azapodophyllotoxin

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X-ray crystal data for 4u; CCDC 614893; Empirical formula C22H22FNO3; Formular weight 367.41; λ = 0.71073 Å; Crystal system = triclinic; Space group P-1; Unit cell dimensions a = 8.467 (6) Å, b = 9.213 (4) Å, c = 12.526 (6) Å, α = 82.806 (6)°, β = 75.484 (6)°, γ = 77.400(6)°; V = 922.7 (7) Å3; z-2; D(calculated) = 1.322 Mg/m3; µ (Mo K α ) = 0.094 mm-1; F(000)-388; Crystal size 0.43 × 0.35 × 0.29 mm; Theta range for data collection 2.27° to 25.01°; R1 = 0.0461, wR2 = 0.0971, S = 1.017; Largest diff. peak and hole 0.183 and -0.161 e Å-3.

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X-ray crystal data for 4kk; CCDC 614892; Empirical formula C26H25NO5; Formula weight 431.47; λ = 0.71073 Å; Crystal system = triclinic; Space group P-1; Unit cell dimensions a = 8.427 (9) Å, b = 11.453 (12) Å, c = 11.579 (12) Å, α = 95.909 (14)°, β = 100.870 (13)°, γ = 94.902 (15)°; V = 1085.3 (19) Å3; z-2, D (Calculated) = 1.320
Mg/m3; µ (MoK α) = 0.092 mm-1; F(000)-456; Crystal size 0.22 × 0.18 × 0.09 mm; Theta range for data collection 1.80° to 25.01°; R1 = 0.0606, wR2 = 0.1227, S = 0.996; Largest diff. peak and hole 0.201 and -0.195 e Å-3.