α-Oxoketene dithioacetal mediated aromatic annulation: highly efficient and concise synthetic routes to potentially carcinogenic polycyclic aromatic hydrocarbons

Nandi, Sukumar ; Panda, Kausik ; Suresh, J. R. ; Ila, Hiriyakkanavar ; Junjappa, Hiriyakkanavar (2004) α-Oxoketene dithioacetal mediated aromatic annulation: highly efficient and concise synthetic routes to potentially carcinogenic polycyclic aromatic hydrocarbons Tetrahedron, 60 (16). pp. 3663-3673. ISSN 0040-4020

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...

Related URL: http://dx.doi.org/10.1016/j.tet.2004.02.053

Abstract

Highly efficient regiospecific routes to potentially carcinogenic polycyclic aromatic hydrocarbons such as substituted benzo[c]phenanthrenes, benzo[c]fluorenes, 16,17-dihydro-11-methyl-15[H]cyclopenta[a]phenanthrene, 5-methyl-7,8,9,10-tetrahydrochrysene and 1,4-dimethylphenanthrene have been developed. The overall strategy involves our aromatic annulation protocol through base induced conjugate addition-elimination on the cyclic and acyclic α-oxoketene dithioacetals with the appropriate arylacetonitriles followed by acid induced cyclodehydration of the resulting conjugate adducts. Subsequent reductive dethiomethylation (Raney Ni) and dehydrogenation (DDQ) of the cyclized products affords the methyl substituted PAHs in high yields.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Polycyclic Aromatic Hydrocarbons; α-Oxoketene Dithioacetals; Aromatic Annulation; Carcinogenic Hydrocarbons; Benzo[c]phenanthrene
ID Code:15322
Deposited On:13 Nov 2010 12:56
Last Modified:22 Feb 2011 06:11

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