A novel one-step efficient method for the synthesis of tetrahydroindoles from 1-(1-pyrrolidino)cyclohexene and chloropyruvates

Tetrahedron Letters

Volumn 49, Issue 31, 2008, Pages 4658-4660

  Mamedov, Vakhid A ^a   Beschastnova, Tatyana N ^a   Zhukova, Nataliya A ^a   Gubaidullin, Aidar T ^a   Isanov, Rustem A ^a   Rizvanov, Ildar Kh ^a  

^a A E ARBUZOV INSTITUTE OF ORGANIC AND PHYSICAL CHEMISTRY   (Russian Federation)

Author keywords

1 (1 Pyrrolidino)cyclohexene; Chloroglycidates; Chloropyruvates; Ring formation; Ring recyclization; Tetrahydroindoles

Indexed keywords

1 (1PYRROLIDINO)CYCLOHEXENE; CHLOROPYRUVATE; CYCLOHEXENE DERIVATIVE; INDOLE DERIVATIVE; PYRUVIC ACID DERIVATIVE; TETRAHYDROINDOLE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 45449105951     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.05.044     Document Type: Article

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45. 2, J = 7.3 Hz); 7.51 (2H, d, aromatics, J = 7.0 Hz); 8.29 (2H, d, aromatics, J = 7.0 Hz). The tetrahydroindoles 3a-d,f-h were obtained in the same way using the corresponding α-chloropyruvates.
46. +{radical dot}35Cl 390 (53); 375(10); 356(32); 355(100); 331(13); 327(10); 313(11); 267(14); 194(10); 91(13); 81(11); 69(16); 55(30); 41(6)).
47. -3). Crystallographic data (except structure factors) for structure 3e in this Letter have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 681280. Copies of these data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK, (fax: +44-(0)1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
48. 3); 6.22 (1H, s, CH); 7.73 (1H, dd, aromatic, J = 8.5, 8.5 Hz); 7.81 (1H, d, aromatic, J = 8.5 Hz); 8.25 (1H, d, aromatic, J = 8.5 Hz); 8.72 (1H, s, aromatic).
49. 1H NMR, IR, MS) of tetrahydroindole 3f obtained from chloropyruvate 2f and chloroglycidate 2f′ were identical as were the mp's 93.5-95 °C.