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A flexible synthesis of 2,3-disubstituted indoles from aminobenzyl phosphonium salts. A direct synthesis of rutaecarpine.
J Org Chem. 2009 Aug 07; 74(15):5337-41.JO

Abstract

The reaction of substituted (2-aminobenzyl)triphenylphosphonium bromides with aromatic aldehydes or alpha,beta-unsaturated aldehydes constitutes a new synthesis of 2,3-disubstitued indoles in high yields. The adduct from 4-oxo-3,4-dihydroquinazoline-2-carbaldehyde was an advanced intermediate in the synthesis of several rutaecarpines.

Authors+Show Affiliations

Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA. gakraus@iastate.eduNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

19527008

Citation

Kraus, George A., and Haitao Guo. "A Flexible Synthesis of 2,3-disubstituted Indoles From Aminobenzyl Phosphonium Salts. a Direct Synthesis of Rutaecarpine." The Journal of Organic Chemistry, vol. 74, no. 15, 2009, pp. 5337-41.
Kraus GA, Guo H. A flexible synthesis of 2,3-disubstituted indoles from aminobenzyl phosphonium salts. A direct synthesis of rutaecarpine. J Org Chem. 2009;74(15):5337-41.
Kraus, G. A., & Guo, H. (2009). A flexible synthesis of 2,3-disubstituted indoles from aminobenzyl phosphonium salts. A direct synthesis of rutaecarpine. The Journal of Organic Chemistry, 74(15), 5337-41. https://doi.org/10.1021/jo900718g
Kraus GA, Guo H. A Flexible Synthesis of 2,3-disubstituted Indoles From Aminobenzyl Phosphonium Salts. a Direct Synthesis of Rutaecarpine. J Org Chem. 2009 Aug 7;74(15):5337-41. PubMed PMID: 19527008.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A flexible synthesis of 2,3-disubstituted indoles from aminobenzyl phosphonium salts. A direct synthesis of rutaecarpine. AU - Kraus,George A, AU - Guo,Haitao, PY - 2009/6/17/entrez PY - 2009/6/17/pubmed PY - 2009/12/16/medline SP - 5337 EP - 41 JF - The Journal of organic chemistry JO - J Org Chem VL - 74 IS - 15 N2 - The reaction of substituted (2-aminobenzyl)triphenylphosphonium bromides with aromatic aldehydes or alpha,beta-unsaturated aldehydes constitutes a new synthesis of 2,3-disubstitued indoles in high yields. The adduct from 4-oxo-3,4-dihydroquinazoline-2-carbaldehyde was an advanced intermediate in the synthesis of several rutaecarpines. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/19527008/A_flexible_synthesis_of_23_disubstituted_indoles_from_aminobenzyl_phosphonium_salts__A_direct_synthesis_of_rutaecarpine_ L2 - https://doi.org/10.1021/jo900718g DB - PRIME DP - Unbound Medicine ER -