Communication

Efficient Synthesis of Tetrasubstituted Furans from Nitroallylic Acetates and 1,3-Dicarbonyl/α-Activating Ketones by Feist–Bénary Addition–Elimination

  1. Wan-Yun Huang,
  2. Yi-Chieh Chen,
  3. Kwunmin Chen*

Article first published online: 1 FEB 2012

DOI: 10.1002/asia.201100988

Issue

Chemistry – An Asian Journal

Chemistry – An Asian Journal

Volume 7, Issue 4, pages 688–691, April 2012

Additional Information

How to Cite

Huang, W.-Y., Chen, Y.-C. and Chen, K. (2012), Efficient Synthesis of Tetrasubstituted Furans from Nitroallylic Acetates and 1,3-Dicarbonyl/α-Activating Ketones by Feist–Bénary Addition–Elimination. Chem. Asian J., 7: 688–691. doi: 10.1002/asia.201100988

Author Information

  1. Chemistry Department, National Taiwan Normal University, 88 Sec. 4, TingChow Rd., Taipei, Taiwan 116, Fax: (+886) 2-9324249

*Chemistry Department, National Taiwan Normal University, 88 Sec. 4, TingChow Rd., Taipei, Taiwan 116, Fax: (+886) 2-9324249

Publication History

  1. Issue published online: 29 MAR 2012
  2. Article first published online: 1 FEB 2012
  3. Manuscript Received: 7 DEC 2011

Funded by

  • National Science Council of the Republic of China. Grant Numbers: NSC 99-2113M-003-002-MY3, NSC 99-2119M-003-001-MY2
  • National Taiwan Normal University. Grant Numbers: 99-D, 100-D-06

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Keywords:

  • addition;
  • elimination;
  • heterocycles;
  • synthetic methods
Thumbnail image of graphical abstract

Pure organic: The synthesis of tetrasubstituted furans often involves transition-metal catalysis or metal–halogen exchange reactions. A new approach to these heterocycles employs the Feist–Bénary addition–elimination process using nitroallylic acetates and 1,3-dicarbonyls (see scheme; X=C, O).

Featured Compounds

Compound 1
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 1a
Molecular Weight:293.272
Molecular Formula:C14H15NO6
InChIKey:GSRUWXGZXHOVCM-FMIVXFBMSA-N
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Compound 2
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 3
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 4
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 5
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 6
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 7
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 4a
Molecular Weight:298.3331
Molecular Formula:C18H18O4
InChIKey:SFMQWARIJDCCPJ-UHFFFAOYSA-N
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Compound 2a
Molecular Weight:112.1265
Molecular Formula:C6H8O2
InChIKey:HJSLFCCWAKVHIW-UHFFFAOYSA-N
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Compound 4b
Molecular Weight:377.229
Molecular Formula:C18H17BrO4
InChIKey:QFUSIRPDMDSCBE-UHFFFAOYSA-N
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Compound 4c
Molecular Weight:328.3591
Molecular Formula:C19H20O5
InChIKey:QJZRSJJBYNBMFN-UHFFFAOYSA-N
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Compound 4d
Molecular Weight:304.361
Molecular Formula:C16H16O4S
InChIKey:ASPGGUVJGWUJCZ-UHFFFAOYSA-N
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Compound 4e
Molecular Weight:288.2952
Molecular Formula:C16H16O5
InChIKey:MDWIISUKSWUUON-UHFFFAOYSA-N
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Compound 4f
Molecular Weight:326.3863
Molecular Formula:C20H22O4
InChIKey:COJVSHUWQDSGNM-UHFFFAOYSA-N
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Compound 4g
Molecular Weight:405.282
Molecular Formula:C20H21BrO4
InChIKey:ASGWHOZKWZIQSV-UHFFFAOYSA-N
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Compound 4h
Molecular Weight:356.4123
Molecular Formula:C21H24O5
InChIKey:ONDVTMREJWEFRS-UHFFFAOYSA-N
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Compound 4i
Molecular Weight:278.3435
Molecular Formula:C16H22O4
InChIKey:ZLWOPCXCYFDUBC-UHFFFAOYSA-N
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Compound 5a
Molecular Weight:348.3487
Molecular Formula:C21H16O5
InChIKey:MQCKVRKDWHXXII-UHFFFAOYSA-N
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Compound 5b
Molecular Weight:382.794
Molecular Formula:C21H15ClO5
InChIKey:VCMDHFNPCWSUSO-UHFFFAOYSA-N
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Compound 5c
Molecular Weight:427.245
Molecular Formula:C21H15BrO5
InChIKey:WJQFDMNOFVVDPT-UHFFFAOYSA-N
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Compound 5d
Molecular Weight:378.3747
Molecular Formula:C22H18O6
InChIKey:ZIBTYIWSOYOPQK-UHFFFAOYSA-N
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Compound 5e
Molecular Weight:354.376
Molecular Formula:C19H14O5S
InChIKey:FDBMBTXLQFPODK-UHFFFAOYSA-N
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Compound 5f
Molecular Weight:338.3109
Molecular Formula:C19H14O6
InChIKey:WGEQDTQWKIUYNC-UHFFFAOYSA-N
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Compound 5g
Molecular Weight:332.3924
Molecular Formula:C22H20O3
InChIKey:ANWJVOWOJJWEBE-UHFFFAOYSA-N
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Compound 5h
Molecular Weight:328.3591
Molecular Formula:C19H20O5
InChIKey:CCMBBKSFZVKYQR-UHFFFAOYSA-N
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Compound 6a
Molecular Weight:331.3646
Molecular Formula:C21H17NO3
InChIKey:UBAKCVFQGNEIDV-UHFFFAOYSA-N
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Compound 6b
Molecular Weight:365.81
Molecular Formula:C21H16ClNO3
InChIKey:XTSLQYBVIBDTDA-UHFFFAOYSA-N
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Compound 6c
Molecular Weight:410.261
Molecular Formula:C21H16BrNO3
InChIKey:PYFGUHUSCWLWAE-UHFFFAOYSA-N
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Compound 6d
Molecular Weight:361.3906
Molecular Formula:C22H19NO4
InChIKey:LGIFUGBMIWGKTL-UHFFFAOYSA-N
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Compound 6e
Molecular Weight:337.392
Molecular Formula:C19H15NO3S
InChIKey:TWMNQVHHBKVDCH-UHFFFAOYSA-N
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Compound 6f
Molecular Weight:321.3267
Molecular Formula:C19H15NO4
InChIKey:HMKKZECELNGUFP-UHFFFAOYSA-N
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Compound 6g
Molecular Weight:311.3749
Molecular Formula:C19H21NO3
InChIKey:UCVGXJSLGSBJIJ-UHFFFAOYSA-N
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Compound 7a
Molecular Weight:286.3224
Molecular Formula:C17H18O4
InChIKey:JVAHCBLFPUZGTA-UHFFFAOYSA-N
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Compound 7b
Molecular Weight:365.218
Molecular Formula:C17H17BrO4
InChIKey:PMUXJWCNVZWSQX-UHFFFAOYSA-N
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Compound 7c
Molecular Weight:316.3484
Molecular Formula:C18H20O5
InChIKey:ZMNDCIZRTAPBNT-UHFFFAOYSA-N
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Compound 7d
Molecular Weight:410.4612
Molecular Formula:C27H22O4
InChIKey:JWSMKADIPYXGCI-UHFFFAOYSA-N
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Compound 7e
Molecular Weight:638.7045
Molecular Formula:C41H34O7
InChIKey:UMFBXJVSSJAANI-UHFFFAOYSA-N
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Compound 8a
Molecular Weight:284.3065
Molecular Formula:C17H16O4
InChIKey:AOFVHHZILLTACG-UHFFFAOYSA-N
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Compound 9a
Molecular Weight:284.3065
Molecular Formula:C17H16O4
InChIKey:FQMGHFVDHQTHAP-UHFFFAOYSA-N
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Compound 9b
Molecular Weight:264.3169
Molecular Formula:C15H20O4
InChIKey:YGRBEMIQMSCKOZ-UHFFFAOYSA-N
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Compound 8b
Molecular Weight:264.3169
Molecular Formula:C15H20O4
InChIKey:SOXHENWAPMWDEE-UHFFFAOYSA-N
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