An abbreviated synthesis of 7,12-dimethylbenz[a]anthracene and benzo[c]chrysene metabolites using the Suzuki reaction

Arun Sharma, Shantu Amin, Subodh Kumar

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Efficient syntheses of important metabolites of 7,12-dimethylbenz[a]anthracene (DMBA) and benzo[c]chrysene (B[c]C), via Suzuki coupling reaction are described. This approach provides an excellent method for the preparation of 3-methoxy-DMBA 5, 10-methoxy-B[c]C 14 and 2-methoxy B[c]C 20, and hence for the corresponding dihydrodiols 6, 15, and 21. Following a similar Suzuki reaction, DMBA-6(5 H)-one 8 was also synthesized in high yield.

Original languageEnglish (US)
Pages (from-to)277-288
Number of pages12
JournalPolycyclic Aromatic Compounds
Volume22
Issue number3-4
DOIs
StatePublished - Jan 1 2002

Fingerprint

Anthracene
Metabolites
9,10-Dimethyl-1,2-benzanthracene
benzo(c)chrysene

All Science Journal Classification (ASJC) codes

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

Cite this

@article{0165a7bbb4e94e67a3702a4e558dc3ee,
title = "An abbreviated synthesis of 7,12-dimethylbenz[a]anthracene and benzo[c]chrysene metabolites using the Suzuki reaction",
abstract = "Efficient syntheses of important metabolites of 7,12-dimethylbenz[a]anthracene (DMBA) and benzo[c]chrysene (B[c]C), via Suzuki coupling reaction are described. This approach provides an excellent method for the preparation of 3-methoxy-DMBA 5, 10-methoxy-B[c]C 14 and 2-methoxy B[c]C 20, and hence for the corresponding dihydrodiols 6, 15, and 21. Following a similar Suzuki reaction, DMBA-6(5 H)-one 8 was also synthesized in high yield.",
author = "Arun Sharma and Shantu Amin and Subodh Kumar",
year = "2002",
month = "1",
day = "1",
doi = "10.1080/10406630290026920",
language = "English (US)",
volume = "22",
pages = "277--288",
journal = "Polycyclic Aromatic Compounds",
issn = "1040-6638",
publisher = "Taylor and Francis Ltd.",
number = "3-4",

}

An abbreviated synthesis of 7,12-dimethylbenz[a]anthracene and benzo[c]chrysene metabolites using the Suzuki reaction. / Sharma, Arun; Amin, Shantu; Kumar, Subodh.

In: Polycyclic Aromatic Compounds, Vol. 22, No. 3-4, 01.01.2002, p. 277-288.

Research output: Contribution to journalArticle

TY - JOUR

T1 - An abbreviated synthesis of 7,12-dimethylbenz[a]anthracene and benzo[c]chrysene metabolites using the Suzuki reaction

AU - Sharma, Arun

AU - Amin, Shantu

AU - Kumar, Subodh

PY - 2002/1/1

Y1 - 2002/1/1

N2 - Efficient syntheses of important metabolites of 7,12-dimethylbenz[a]anthracene (DMBA) and benzo[c]chrysene (B[c]C), via Suzuki coupling reaction are described. This approach provides an excellent method for the preparation of 3-methoxy-DMBA 5, 10-methoxy-B[c]C 14 and 2-methoxy B[c]C 20, and hence for the corresponding dihydrodiols 6, 15, and 21. Following a similar Suzuki reaction, DMBA-6(5 H)-one 8 was also synthesized in high yield.

AB - Efficient syntheses of important metabolites of 7,12-dimethylbenz[a]anthracene (DMBA) and benzo[c]chrysene (B[c]C), via Suzuki coupling reaction are described. This approach provides an excellent method for the preparation of 3-methoxy-DMBA 5, 10-methoxy-B[c]C 14 and 2-methoxy B[c]C 20, and hence for the corresponding dihydrodiols 6, 15, and 21. Following a similar Suzuki reaction, DMBA-6(5 H)-one 8 was also synthesized in high yield.

UR - http://www.scopus.com/inward/record.url?scp=0036401214&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0036401214&partnerID=8YFLogxK

U2 - 10.1080/10406630290026920

DO - 10.1080/10406630290026920

M3 - Article

AN - SCOPUS:0036401214

VL - 22

SP - 277

EP - 288

JO - Polycyclic Aromatic Compounds

JF - Polycyclic Aromatic Compounds

SN - 1040-6638

IS - 3-4

ER -