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Syntheses of isochromenes and naphthalenes by electrophilic cyclization of acetylenic arenecarboxaldehydes.
J Org Chem. 2006 Apr 28; 71(9):3381-8.JO

Abstract

Highly substituted 1H-isochromenes, isobenzofurans, and pyranopyridines can be prepared by allowing o-(1-alkynyl)arenecarboxaldehydes and ketones to react with I2, ICl, NIS, Br2, NBS, p-O2NC6H4SCl, or PhSeBr and various alcohols or carbon-based nucleophiles at room temperature. Naphthyl ketones and iodides are also readily prepared by the reaction of 2-(1-alkynyl)arenecarboxaldehydes with I2 and simple olefins or alkynes.

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Authors+Show Affiliations

Yue D
Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
Della Ca N
No affiliation info available
Larock RC
No affiliation info available

MeSH

AcetyleneAldehydesBenzopyransCyclizationNaphthalenes

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

16626117

Citation

Yue, Dawei, et al. "Syntheses of Isochromenes and Naphthalenes By Electrophilic Cyclization of Acetylenic Arenecarboxaldehydes." The Journal of Organic Chemistry, vol. 71, no. 9, 2006, pp. 3381-8.
Yue D, Della Ca N, Larock RC. Syntheses of isochromenes and naphthalenes by electrophilic cyclization of acetylenic arenecarboxaldehydes. J Org Chem. 2006;71(9):3381-8.
Yue, D., Della Ca, N., & Larock, R. C. (2006). Syntheses of isochromenes and naphthalenes by electrophilic cyclization of acetylenic arenecarboxaldehydes. The Journal of Organic Chemistry, 71(9), 3381-8.
Yue D, Della Ca N, Larock RC. Syntheses of Isochromenes and Naphthalenes By Electrophilic Cyclization of Acetylenic Arenecarboxaldehydes. J Org Chem. 2006 Apr 28;71(9):3381-8. PubMed PMID: 16626117.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Syntheses of isochromenes and naphthalenes by electrophilic cyclization of acetylenic arenecarboxaldehydes. AU - Yue,Dawei, AU - Della Ca,Nicola, AU - Larock,Richard C, PY - 2006/4/22/pubmed PY - 2007/5/10/medline PY - 2006/4/22/entrez SP - 3381 EP - 8 JF - The Journal of organic chemistry JO - J Org Chem VL - 71 IS - 9 N2 - Highly substituted 1H-isochromenes, isobenzofurans, and pyranopyridines can be prepared by allowing o-(1-alkynyl)arenecarboxaldehydes and ketones to react with I2, ICl, NIS, Br2, NBS, p-O2NC6H4SCl, or PhSeBr and various alcohols or carbon-based nucleophiles at room temperature. Naphthyl ketones and iodides are also readily prepared by the reaction of 2-(1-alkynyl)arenecarboxaldehydes with I2 and simple olefins or alkynes. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/16626117/Syntheses_of_isochromenes_and_naphthalenes_by_electrophilic_cyclization_of_acetylenic_arenecarboxaldehydes_ DB - PRIME DP - Unbound Medicine ER -