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Synthesis 2010(20): 3520-3535  
DOI: 10.1055/s-0030-1257974
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Naphtho- and Benzo[g]quinoxalino-Fused Oxazocinoquinolinones and Their Diaryl and Alkynyl Analogues from Quinolin-8-ols: A Library of Novel Polynuclear Heteroaromatics

Rupankar Paira, Arindam Maity, Subhendu Naskar, Shyamal Mondal, Priyankar Paira, Abhijit Hazra, Krishnendu B. Sahu, Pritam Saha, Sukdeb Banerjee, Nirup B. Mondal*
Department of Chemistry, Indian Institute of Chemical Biology, Council of Scientific and Industrial Research, 4 Raja S. C. Mullick Road, Jadavpur, Kolkata 700032, India
Fax: +91(33)24735197; e-Mail: nirup@iicb.res.in;
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Publication History

Received 15 june 2010
Publication Date:
04 August 2010 (online)

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Abstract

The efficient syntheses of 6,6,8,6,6-pentacyclic naphtho-fused oxazocinoquinolinones and 6,6,8,6,6,6-hexacyclic benzo[g]quinoxalino-fused oxazocinoquinolinones were achieved in one-pot sequences. The generation of libraries of their diaryl- and alkynyl-substituted analogues via Suzuki-Miyaura and Sonogashira cross-coupling reactions, respectively, were also achieved.

Key words

fused-ring systems - oxazocinoquinolinones - diarylations - alkynylations - cross-coupling

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20

For the single-crystal X-ray crystallographic analysis of compound 3a (C21H15NO2), yellowish needle-shaped crystals were grown from CHCl3-MeCN (7:3); monoclinic, space group P2(1)/n; unit cell parameters: a = 14.102(5), b = 15.073(5), c = 15.994(6). Diffraction data were measured with MoKα (0.71073 Å) radiation at 296 K using a Kappa Apex 2 instrument. The structure was solved by direct methods using the SHELX-97 program. Refinements of F ² were carried out against all reflections using SHELX-97.

21

For the single-crystal X-ray crystallographic analysis of compound 11a (C25H16ClNO2), yellowish block-shaped crystals were grown from CHCl3-MeCN (9:1); triclinic, space group P1; unit cell parameters: a = 9.1980(7), b = 10.0460(8), c = 10.9903(9), α = 70.913(3), β = 87.778(3), γ = 79.707(2). Diffraction data were measured with MoKα (0.71073 Å) radiation at 296 K using a Kappa Apex 2 instrument. The structure was solved by direct methods using the SHELX-97 program. Refinements of F ² were carried out against all reflections using SHELX-97.