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2 article(s) from Masesane, Ishmael B

Reactions of salicylaldehyde and enolates or their equivalents: versatile synthetic routes to chromane derivatives

Ishmael B. Masesane and
Zelalem Yibralign Desta

Beilstein J. Org. Chem. 2012, 8, 2166–2175, doi:10.3762/bjoc.8.244

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Graphical Abstract

Scheme 1: Retrosynthetic analysis of chromane 1.

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Scheme 2: General reaction of salicylaldehyde (5) and acetophenone (7) in the synthesis of flavan 10 and flav...

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Scheme 3: Synthesis of flavan 16 by Xue and co-workers.

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Scheme 4: Synthesis of flavans of type 10 by Mazimba and co-workers.

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Scheme 5: Sashidhara and co-workers synthesis of flavone (11).

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Scheme 6: Synthesis of chromane derivative 19 by Yu-Ling and co-workers.

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Scheme 7: Synthesis of 2-iminochromene 21 by Costa and co-workers.

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Scheme 8: Synthesis of 2-aminochromene 22 by Costa and co-workers.

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Scheme 9: Costa and co-workers used Et₃N in the synthesis of 2-aminochromene 24.

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Scheme 10: Synthesis of 2-aminochromene 27 by Shanthi and co-workers.

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Scheme 11: Enantioselective synthesis of 2-aminochromenes 32–34 by Yang and co-workers.

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Scheme 12: Synthesis of 2-iminochromene derivatives of type 36 by Kovalenko and co-workers.

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Scheme 13: Synthesis of 2-aminochromenes 22 and 37 by Ghorbani-Vaghei and co-workers.

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Scheme 14: Synthesis of 2-aminochromene 39 by Yu and co-workers.

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Scheme 15: Synthesis of 2-iminochromene 21 by Heravi and co-workers.

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Scheme 16: Tandem reaction of salicylaldehyde and α,β-unsaturated compounds.

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Scheme 17: Kawase and co-workers synthesis of 2,2-dimethylchromene 45.

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Scheme 18: Synthesis of 2,3-disubstituted chromene 47 by Stukan and co-workers.

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Scheme 19: Ravichandrans synthesis of 3-substituted chromenes 52–55.

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Scheme 20: Synthesis of 3-substituted chromene 58 coumarin 59 by Paye and co-workers.

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Scheme 21: Govender and co-workers asymmetric synthesis of 2-phenylchromenes 62 and 63.

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Scheme 22: Asymmetric synthesis of 2-phenylchromene 62 by Li and co-workers.

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Review

Published 12 Dec 2012

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The oxanorbornene approach to 3-hydroxy, 3,4-dihydroxy and 3,4,5-trihydroxy derivatives of 2-aminocyclohexanecarboxylic acid

Ishmael B. Masesane,
Andrei S. Batsanov,
Judith A. K. Howard,
Raju Mondal and
Patrick G. Steel

Beilstein J. Org. Chem. 2006, 2, No. 9, doi:10.1186/1860-5397-2-9

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Scheme 1: The furan-nitroacylate approach to poly hydroxylated ACHC derivatives

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Scheme 2: Reagents: i. Furan (see box); ii. Zn, HCl., EtOH then Boc₂O, Et₃N, 2b 89%, 3b 77%; iii. KHMDS, THF,...

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Figure 1: Selected NOESY Correlations for 6–9

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Scheme 3: Reagents: i. mCPBA, CH₂Cl₂ 11 : 12 (9 : 1) 77%, 15 82%; ii. Ac₂O, Py then mCPBA, CH₂Cl₂ (13 only) 6...

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Figure 2: Selected NOESY Correlations for 14–16 (R = Boc)

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Scheme 4: Reagents: i. OsO₄, Me₃NO.H₂O, acetone 18 78% from 4 ii. TBSCl, imidazole, CH₂Cl₂, 17 66% from 2b; i...

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Figure 3: Selected NOESY correlations for 24 – 26

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Scheme 5: Reagents: i. HClO₄, H₂O/acetone; v. Ac₂O, pyridine; iii. H₂, Pd/C, 24 71%, 25 67%, 26 71%

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Full Research Paper

Published 04 May 2006

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