Cyclizations of phenylethyl-substituted pyridinecarboxaldehydes

Rajasekhar Reddy Naredla; Douglas A. Klumpp

doi:10.1016/j.tet.2013.01.004

Cyclizations of phenylethyl-substituted pyridinecarboxaldehydes

Rajasekhar Reddy Naredla, Douglas A. Klumpp

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

Abstract

Several phenylethyl-substituted pyridinecarboxaldehydes were prepared from 2-bromo-3-pyridine-carboxaldehyde and these substances are found to undergo cyclization reactions in acidic media. In the absence of added nucleophile, acid-promoted cyclization and oxidation (MnO₂) provide an efficient route to 10,11-dihydro-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-ones. Arene nucleophiles may also be added to the acidic mixture to provide good yields of triarylmethane products. Mechanisms are proposed involving dicationic superelectrophilic intermediates.

Original language	English (US)
Pages (from-to)	2137-2141
Number of pages	5
Journal	Tetrahedron
Volume	69
Issue number	9
DOIs	https://doi.org/10.1016/j.tet.2013.01.004
State	Published - Mar 4 2013
Externally published	Yes

Keywords

Cycloheptabenzopyridine
Friedel-Crafts
Heterocycle
Superacid
Superelectrophile

Publisher link

10.1016/j.tet.2013.01.004

Find It

Find It at U of M Libraries

Cite this

@article{aa0a03d0e3e04e84b1a8edfb585e1dd9,

title = "Cyclizations of phenylethyl-substituted pyridinecarboxaldehydes",

abstract = "Several phenylethyl-substituted pyridinecarboxaldehydes were prepared from 2-bromo-3-pyridine-carboxaldehyde and these substances are found to undergo cyclization reactions in acidic media. In the absence of added nucleophile, acid-promoted cyclization and oxidation (MnO2) provide an efficient route to 10,11-dihydro-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-ones. Arene nucleophiles may also be added to the acidic mixture to provide good yields of triarylmethane products. Mechanisms are proposed involving dicationic superelectrophilic intermediates.",

keywords = "Cycloheptabenzopyridine, Friedel-Crafts, Heterocycle, Superacid, Superelectrophile",

author = "Naredla, {Rajasekhar Reddy} and Klumpp, {Douglas A.}",

year = "2013",

month = mar,

day = "4",

doi = "10.1016/j.tet.2013.01.004",

language = "English (US)",

volume = "69",

pages = "2137--2141",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "9",

}

TY - JOUR

T1 - Cyclizations of phenylethyl-substituted pyridinecarboxaldehydes

AU - Naredla, Rajasekhar Reddy

AU - Klumpp, Douglas A.

PY - 2013/3/4

Y1 - 2013/3/4

N2 - Several phenylethyl-substituted pyridinecarboxaldehydes were prepared from 2-bromo-3-pyridine-carboxaldehyde and these substances are found to undergo cyclization reactions in acidic media. In the absence of added nucleophile, acid-promoted cyclization and oxidation (MnO2) provide an efficient route to 10,11-dihydro-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-ones. Arene nucleophiles may also be added to the acidic mixture to provide good yields of triarylmethane products. Mechanisms are proposed involving dicationic superelectrophilic intermediates.

AB - Several phenylethyl-substituted pyridinecarboxaldehydes were prepared from 2-bromo-3-pyridine-carboxaldehyde and these substances are found to undergo cyclization reactions in acidic media. In the absence of added nucleophile, acid-promoted cyclization and oxidation (MnO2) provide an efficient route to 10,11-dihydro-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-ones. Arene nucleophiles may also be added to the acidic mixture to provide good yields of triarylmethane products. Mechanisms are proposed involving dicationic superelectrophilic intermediates.

KW - Cycloheptabenzopyridine

KW - Friedel-Crafts

KW - Heterocycle

KW - Superacid

KW - Superelectrophile

UR - http://www.scopus.com/inward/record.url?scp=84873281931&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84873281931&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2013.01.004

DO - 10.1016/j.tet.2013.01.004

M3 - Article

AN - SCOPUS:84873281931

SN - 0040-4020

VL - 69

SP - 2137

EP - 2141

JO - Tetrahedron

JF - Tetrahedron

IS - 9

ER -

Cyclizations of phenylethyl-substituted pyridinecarboxaldehydes

Abstract

Keywords

Publisher link

Find It

Other files and links

Fingerprint

Cite this