Cleavage of some annulated tetrahydropyridines under the action of dimethyl acetylene dicarboxylate in protic solvents. New practical route to substituted pyrroles and indoles

Molecular Diversity

Volumn 6, Issue 3-4, 2003, Pages 207-212

  Borisova, Tatiana N ^a   Voskressensky, Leonid G ^a   Soklakova, Tatiana A ^a   Kulikova, Larisa N ^a   Varlamov, Alexey V ^a  

^a PEOPLES FRIENDSHIP UNIVERSITY OF RUSSIA   (Russian Federation)

Author keywords

Cleavage; Indole; Pyridines; Pyrrole; Tandem reactions

Indexed keywords

ACETYLENEDICARBOXYLIC ACID DIMETHYL ESTER; ALCOHOL; INDOLE DERIVATIVE; PROTON; PYRIDINE DERIVATIVE; PYRROLE DERIVATIVE; SOLVENT; TETRAHYDROPYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; CONFERENCE PAPER; PRIORITY JOURNAL; PRODUCTIVITY; REACTION ANALYSIS; RING OPENING; ROOM TEMPERATURE;

ACETYLENE; ALCOHOLS; CARBOXYLIC ACIDS; DIOXANES; INDOLES; MOLECULAR STRUCTURE; PIPERIDINES; PYRIDINES; PYRROLES; SOLVENTS;

EID: 0345871012     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:MODI.0000006760.30731.46     Document Type: Conference Paper

References (7)

1. a) For a recent review on THPP chemistry, see: Varlamov, A. V., Borisova, T. N. and Voskressensky, L. G. Hydrogenated pyrrolopyridines. Synthesis and reactivity. Synthesis, 2 (2002) 155-168.
2. For THPP 5-15 and THPI 16 synthesis see: Voskressensky, L. G., de Candia, M., Carotti, A., Borisova, T. N., Kulikova, L. N., Varlamov, A. V. and Altomare, C. Investigation on the antiplatelet activity of pyrrolo[3,2-c]pyridine-containing compounds JPP, 55 (2003) 323-332.
3. Varlamov, A. V., Borisova, T. N., Voskressensky, L. G., Nsabimana, B. and Chernyshev, A. I., Tandem Michael addition-Hoffman elimination sequence of DMAD on tetrahydropyrrolo[3,2-c]pyridines. New route to vinylpyrroles, Heterocycl. Commun., 7 (2001) 461-465.
4. Varlamov, A. V., Borisova, T. N., Voskressensky, L. G., Kulikova, L. N., Soklakova, T. A., Chemyshev, A. I. and Alexandrov, G. G., The first synthsesis and X-ray crystal structure of tetrahydropyrrolo[2.3-d]azocines Tetrahedron lett., 43 (2002), 6767-6769.
5. Aliev, A. E., Sinitsyna, A. A., Borisova, T. N., Stazharova, I. A., Prostakov, N. S. and Varlamov, A. V. Carbon-13 and proton NMR study of the stereochemistry of N-unsubstituted and N-vinyl-4,5,7-trimethyl-4,5,6,7-tetrahydropyrrolo[3,2-c]pyridines and their nitro derivatives, Chem. Heterocycl. Compd. (Engl. Transl.), 29 (1993) 65-71.
6. Sheldrick, G. M. SHELXS, program for crystal structure solution, University of Göttingen, Germany, 1997.
7. Sheldrick, G. M. SHELXL, program for crystal structure refinement, University of Göttingen, Germany, 1997.