Tags

Type your tag names separated by a space and hit enter

Tandem synthesis of pyrroloacridones via [3 + 2] alkyne annulation/ring-opening with concomitant intramolecular aldol condensation.
J Org Chem. 2013 Jun 07; 78(11):5372-84.JO

Abstract

An efficient cascade strategy for the direct synthesis of pyrrolo[3,2,1-de]acridones 4a-v, 5a-h from iodo-pyranoquinolines 2a-i by the palladium-catalyzed regioselective [3 + 2] alkyne annulation/ring-opening followed by intramolecular aldol condensation under microwave irradiation is described. The chemistry involves the in situ formation of pyrroloquinolines Y, via palladium-catalyzed selective [3 + 2] annulation of iodopyranoquinolines and internal akynes with ring-opening and successive intramolecular cross-aldol condensation. Both the symmetrical and unsymmetrical internal alkynes were reacted smoothly to provide the desired pyrroloacridones in good yields. This methodology provides the facile conversion of easily accessble iodopyranoquinoline into highly functionalized biologically important pyrroloacridones in a single process.

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Verma AK
Synthetic Organic Chemistry Laboratory, Department of Chemistry, University of Delhi, Delhi, 110007, India.
Kotla SK
No affiliation info available
Aggarwal T
No affiliation info available
Kumar S
No affiliation info available
Nimesh H
No affiliation info available
Tiwari RK
No affiliation info available

MeSH

AcridinesAldehydesAlkynesCyclizationMicrowavesMolecular StructurePyrroles

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

23642218

Citation

Verma, Akhilesh K., et al. "Tandem Synthesis of Pyrroloacridones Via [3 + 2] Alkyne Annulation/ring-opening With Concomitant Intramolecular Aldol Condensation." The Journal of Organic Chemistry, vol. 78, no. 11, 2013, pp. 5372-84.
Verma AK, Kotla SK, Aggarwal T, et al. Tandem synthesis of pyrroloacridones via [3 + 2] alkyne annulation/ring-opening with concomitant intramolecular aldol condensation. J Org Chem. 2013;78(11):5372-84.
Verma, A. K., Kotla, S. K., Aggarwal, T., Kumar, S., Nimesh, H., & Tiwari, R. K. (2013). Tandem synthesis of pyrroloacridones via [3 + 2] alkyne annulation/ring-opening with concomitant intramolecular aldol condensation. The Journal of Organic Chemistry, 78(11), 5372-84. https://doi.org/10.1021/jo400539x
Verma AK, et al. Tandem Synthesis of Pyrroloacridones Via [3 + 2] Alkyne Annulation/ring-opening With Concomitant Intramolecular Aldol Condensation. J Org Chem. 2013 Jun 7;78(11):5372-84. PubMed PMID: 23642218.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Tandem synthesis of pyrroloacridones via [3 + 2] alkyne annulation/ring-opening with concomitant intramolecular aldol condensation. AU - Verma,Akhilesh K, AU - Kotla,Siva K Reddy, AU - Aggarwal,Trapti, AU - Kumar,Sonu, AU - Nimesh,Hemlata, AU - Tiwari,Rakesh K, Y1 - 2013/05/14/ PY - 2013/5/7/entrez PY - 2013/5/7/pubmed PY - 2013/12/20/medline SP - 5372 EP - 84 JF - The Journal of organic chemistry JO - J Org Chem VL - 78 IS - 11 N2 - An efficient cascade strategy for the direct synthesis of pyrrolo[3,2,1-de]acridones 4a-v, 5a-h from iodo-pyranoquinolines 2a-i by the palladium-catalyzed regioselective [3 + 2] alkyne annulation/ring-opening followed by intramolecular aldol condensation under microwave irradiation is described. The chemistry involves the in situ formation of pyrroloquinolines Y, via palladium-catalyzed selective [3 + 2] annulation of iodopyranoquinolines and internal akynes with ring-opening and successive intramolecular cross-aldol condensation. Both the symmetrical and unsymmetrical internal alkynes were reacted smoothly to provide the desired pyrroloacridones in good yields. This methodology provides the facile conversion of easily accessble iodopyranoquinoline into highly functionalized biologically important pyrroloacridones in a single process. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/23642218/Tandem_synthesis_of_pyrroloacridones_via_[3_+_2]_alkyne_annulation/ring_opening_with_concomitant_intramolecular_aldol_condensation_ DB - PRIME DP - Unbound Medicine ER -