Tags

Type your tag names separated by a space and hit enter

Synthesis of dibenzocyclohepten-5-ones by electrophilic iodocyclization of 1-([1,1'-biphenyl]-2-yl)alkynones.
J Org Chem. 2014 Apr 18; 79(8):3452-64.JO

Abstract

A synthesis of iodo-substituted dibenzocyclohepten-5-ones by the iodine monochloride (or iodine)-induced intramolecular 7-endo-dig cyclization of 1-([1,1'-biphenyl]-2-yl)alkynones is reported. Detailed investigations on the substituent effects during the electrophilic iodocyclization of the alkynones show that they play a crucial role in determining the reaction pathways of the cyclization. By modifying the substitution pattern on the alkynone substrates, the cyclization takes place regioselectively, leading to either dibenzocyclohepten-5-ones, via a 7-endo-dig cyclization, or spiroconjugated compounds, via a 6-endo-dig cyclization.

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Chen Y
Department of Chemistry and Biochemistry, Queens College and the Graduate Center of the City University of New York , 65-30 Kissena Boulevard, Flushing, New York 11367, United States.
Huang C
No affiliation info available
Liu X
No affiliation info available
Perl E
No affiliation info available
Chen Z
No affiliation info available
Namgung J
No affiliation info available
Subramaniam G
No affiliation info available
Zhang G
No affiliation info available
Hersh WH
No affiliation info available

MeSH

AlkynesCatalysisCyclizationCycloheptanesIodineMolecular StructureStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

24641681

Citation

Chen, Yu, et al. "Synthesis of Dibenzocyclohepten-5-ones By Electrophilic Iodocyclization of 1-([1,1'-biphenyl]-2-yl)alkynones." The Journal of Organic Chemistry, vol. 79, no. 8, 2014, pp. 3452-64.
Chen Y, Huang C, Liu X, et al. Synthesis of dibenzocyclohepten-5-ones by electrophilic iodocyclization of 1-([1,1'-biphenyl]-2-yl)alkynones. J Org Chem. 2014;79(8):3452-64.
Chen, Y., Huang, C., Liu, X., Perl, E., Chen, Z., Namgung, J., Subramaniam, G., Zhang, G., & Hersh, W. H. (2014). Synthesis of dibenzocyclohepten-5-ones by electrophilic iodocyclization of 1-([1,1'-biphenyl]-2-yl)alkynones. The Journal of Organic Chemistry, 79(8), 3452-64. https://doi.org/10.1021/jo5001803
Chen Y, et al. Synthesis of Dibenzocyclohepten-5-ones By Electrophilic Iodocyclization of 1-([1,1'-biphenyl]-2-yl)alkynones. J Org Chem. 2014 Apr 18;79(8):3452-64. PubMed PMID: 24641681.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of dibenzocyclohepten-5-ones by electrophilic iodocyclization of 1-([1,1'-biphenyl]-2-yl)alkynones. AU - Chen,Yu, AU - Huang,Chenlong, AU - Liu,Xiaochen, AU - Perl,Eliyahu, AU - Chen,Zhiwei, AU - Namgung,Jieun, AU - Subramaniam,Gopal, AU - Zhang,Gan, AU - Hersh,William H, Y1 - 2014/03/31/ PY - 2014/3/20/entrez PY - 2014/3/20/pubmed PY - 2014/11/6/medline SP - 3452 EP - 64 JF - The Journal of organic chemistry JO - J Org Chem VL - 79 IS - 8 N2 - A synthesis of iodo-substituted dibenzocyclohepten-5-ones by the iodine monochloride (or iodine)-induced intramolecular 7-endo-dig cyclization of 1-([1,1'-biphenyl]-2-yl)alkynones is reported. Detailed investigations on the substituent effects during the electrophilic iodocyclization of the alkynones show that they play a crucial role in determining the reaction pathways of the cyclization. By modifying the substitution pattern on the alkynone substrates, the cyclization takes place regioselectively, leading to either dibenzocyclohepten-5-ones, via a 7-endo-dig cyclization, or spiroconjugated compounds, via a 6-endo-dig cyclization. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/24641681/Synthesis_of_dibenzocyclohepten_5_ones_by_electrophilic_iodocyclization_of_1__[11'_biphenyl]_2_yl_alkynones_ DB - PRIME DP - Unbound Medicine ER -