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. 2019 Aug 6;9(42):24314-24318.
doi: 10.1039/c9ra02590a. eCollection 2019 Aug 2.

Two step, one-pot sequential synthesis of functionalized hybrid polyheterocyclic scaffolds via a solid state melt reaction (SSMR)

Manickam Bakthadoss  1 , Jayakumar Srinivasan  1 , Mir Ashiq Hussain  1 , Duddu S Sharada  2
Affiliations

Two step, one-pot sequential synthesis of functionalized hybrid polyheterocyclic scaffolds via a solid state melt reaction (SSMR)

Manickam Bakthadoss et al. RSC Adv. .

Abstract

A new one pot assembly of highly functionalized benzo[a]phenazinone fused chromene/bicyclic scaffolds via a domino Knoevenagel intramolecular hetero-Diels-Alder (IMHDA) strategy using a solid state melt reaction (SSMR) of 2-hydroxynaphthalene 1,4-dione, o-phenylenediamine, O-allyl salicylaldehyde/O-vinyl salicylaldehyde derivatives is reported. The formation of five new bonds (two C-C bonds and three C-O bonds), three six-membered rings, and three stereogenic centers in a one-pot manner is very attractive. Ease of reaction with short time, good yields with water as the only byproduct and work up free procedure are some of the excellent features of the present protocol.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. Some of naturally occurring phenazine derivatives.
Scheme 1
Scheme 1. Synthetic approach to benzo[a]phenazinone fused chromenes.
Fig. 2
Fig. 2. Competitive two different heterodienes present in the intermediate.
Fig. 3
Fig. 3. X-ray crystal structure of 4l and 8b.
See this image and copyright information in PMC

References

    1. For some reviews on MC reactions, see:

    2. Armstrong R. M. Combs A. P. Brown P. A. Keating T. A. Acc. Chem. Res. 1996;29:123–131. doi: 10.1021/ar9502083. - DOI
    3. Dömling A. Ugi I. Angew. Chem., Int. Ed. 2000;39:3169–3210. doi: 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO;2-U. - DOI - PubMed
    4. Bienaymé H. Hulme C. Oddon G. Schmitt P. Chem. –Eur. J. 2000;6:3321–3329. doi: 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO;2-A. - DOI - PubMed
    5. Dömling A. Curr. Opin. Chem. Biol. 2000;4:318–323. doi: 10.1016/S1367-5931(00)00095-8. - DOI - PubMed
    6. Dömling A. Chem. Rev. 2006;106:17–89. doi: 10.1021/cr0505728. - DOI - PubMed
    7. Isambert N. Lavilla R. Chem. –Eur. J. 2008;14:8444–8454. doi: 10.1002/chem.200800473. - DOI - PubMed
    8. Ganem B. Acc. Chem. Res. 2009;42:463–472. doi: 10.1021/ar800214s. - DOI - PMC - PubMed
    9. Ruijter E. Scheffelaar R. Orru R. V. Angew. Chem., Int. Ed. 2011;50:6234–6246. doi: 10.1002/anie.201006515. - DOI - PubMed
    1. Andraos J. Org. Process Res. Dev. 2005;9:149–163. doi: 10.1021/op049803n. - DOI
    1. Doemling A. Ugi I. Angew. Chem., Int. Ed. Engl. 2000;39:3169–3210. - PubMed
    2. Bienaymé H. Hulme C. Oddon G. Schmitt P. Chem.–Eur. J. 2000;6:3321–3329. doi: 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO;2-A. - DOI - PubMed
    1. Dictionary of Alkaloids, ed., I. W.Southon and J.Buckingham, Chapman & Hall, New York, 1989
    1. Laursen J. B. Nielsen J. Chem. Rev. 2004;104:1663–1686. doi: 10.1021/cr020473j. - DOI - PubMed
    2. Makgatho M. Anderson R. O'Sullivan J. Egan T. Freese J. Cornelius N. Van Rensburg C. Drug Dev. Res. 2000;50:195–202. doi: 10.1002/1098-2299(200006)50:2<195::AID-DDR10>3.0.CO;2-T. - DOI
    3. Andrade-Nieto V. Goulart M. da Silva J. F. da Silva M. J. Pinto M. Pinto A. Zalis M. Carvalho L. Krettli A. Bioorg. Med. Chem. Lett. 2004;14:1145–1149. doi: 10.1016/j.bmcl.2003.12.069. - DOI - PubMed
    4. Neves-Pinto C. Malta V. Pinto M. Santos R. Castro S. Pinto A. J. Med. Chem. 2002;45:740–743. doi: 10.1021/jm010377v. - DOI - PubMed
    5. Cartwright D. Chilton W. Benson D. Appl. Microbiol. Biotechnol. 1995;43:211–216. doi: 10.1007/BF00172814. - DOI
    6. Ligon J. Dwight S. Hammer P. Torkewitz N. Hofmann D. Kempf H. Pee K. Pest Manage. Sci. 2000;56:688–695. doi: 10.1002/1526-4998(200008)56:8<688::AID-PS186>3.0.CO;2-V. - DOI
    7. Muller M. Sorrell T. Prostaglandins. 1995;50:301–311. doi: 10.1016/0090-6980(95)00133-6. - DOI - PubMed