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DOI: 10.1055/s-0029-1218731
Regioselective Synthesis of Highly Functionalized 3-Spiropyrrolidine/pyrrolizidine Oxindoles and Acenaphthenones via One-Pot Four-Component [3+2] Cycloaddition
Publication History
Publication Date:
12 April 2010 (online)
Abstract
A facile and efficient entry into highly functionalized 3-spiropyrrolidine oxindoles and 3-spiropyrrolizidine oxindoles, as well as to 3-spiropyrrolidine acenaphthenones via one-pot four-component reactions of 3-cyanoacetylindoles, aldehydes, isatin/acenaphthylene-1,2-dione and amino acid has been developed. Particularly valuable features of this method include high yields of products, broad substrate scope and a straightforward procedure.
Key words
multicomponent [3+2] cycloaddition - spirooxindoles - one-pot synthesis - indole-containing heterocycles
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References
Structural parameters for 5b (CCDC 760960): Data collection: Rigaku Mercury CCD area detector; empirical formula: C56H42Cl2N8O4; colorless solid; crystal dimensions: 0.55 × 0.50 × 0.15 mm; orthorhombic; space group: Pna21; unit cell dimensions: a = 16.2592(11) Å, b = 11.3924(9) Å, c = 25.3133(19) Å; V = 4688.8(6) ų; Mr 961.88; Z = 4; D(calcd) = 1.363 Mg/m³; λ (Mo-Kα) = 0.71075 Å; µ = 0.197 mm-¹; F(000) = 2000, 3.00˚ < θ < 25.49˚, R [I>2 σ ( I)] = 0.0532, wR [I>2 σ ( I)] = 0.1221; largest diff. peak and hole: 0.270 and -0.274 e Å-³.
19Structural parameters for 5f (CCDC 760959): Data collection: Rigaku Mercury CCD area detector; empirical formula: C28H22N4O2; colorless solid; crystal dimensions: 0.60 × 0.55 × 0.18 mm; monoclinic; space group P 21/c; unit cell dimensions: a = 25.720 (5) Å, b = 11.1847(18) Å, c = 16.399(3) Å, β = 105.649(5)˚; V = 4542.7(14) ų; Mr = 446.50; Z = 8; D(calcd) = 1.306 Mg/m³; λ (Mo-Kα) = 0.71075 Å; µ = 0.084 mm-¹; F(000) = 1872, 3.05˚ < θ < 25.50˚, R [I>2s ( I)] = 0.0790, wR [I>2s ( I)] = 0.2030; largest diff. peak and hole: 0.397 and -0.269 e Å-³.