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Lewis acid catalyzed cascade reaction of 3-(2-benzenesulfonamide)propargylic alcohols to spiro[indene-benzosultam]s.
Org Lett. 2015 Jan 16; 17(2):242-5.OL

Abstract

A highly efficient and convenient construction of the spiro[indene-benzosultam] skeleton from propargylic alcohols has been developed. The reaction proceeded in a Lewis acid catalyzed cascade process, including the trapping of allene carbocation with sulfonamide, electrophilic cyclization, and intramolecular Friedel-Crafts alkylation. In the presence of NIS or NBS, iodo/bromo-substituted spiro[indene-benzosultam]s could be prepared in excellent yields.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Sun L
Department of Chemistry, Zhejiang University , Hangzhou 310027, P. R. China.
Zhu Y
No affiliation info available
Wang J
No affiliation info available
Lu P
No affiliation info available
Wang Y
No affiliation info available

MeSH

AlcoholsAlkenesAlkylationCatalysisCyclizationIndenesLewis AcidsMolecular StructureSulfonamides

Pub Type(s)

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

Language

eng

PubMed ID

25541815

Citation

Sun, Lang, et al. "Lewis Acid Catalyzed Cascade Reaction of 3-(2-benzenesulfonamide)propargylic Alcohols to Spiro[indene-benzosultam]s." Organic Letters, vol. 17, no. 2, 2015, pp. 242-5.
Sun L, Zhu Y, Wang J, et al. Lewis acid catalyzed cascade reaction of 3-(2-benzenesulfonamide)propargylic alcohols to spiro[indene-benzosultam]s. Org Lett. 2015;17(2):242-5.
Sun, L., Zhu, Y., Wang, J., Lu, P., & Wang, Y. (2015). Lewis acid catalyzed cascade reaction of 3-(2-benzenesulfonamide)propargylic alcohols to spiro[indene-benzosultam]s. Organic Letters, 17(2), 242-5. https://doi.org/10.1021/ol503316e
Sun L, et al. Lewis Acid Catalyzed Cascade Reaction of 3-(2-benzenesulfonamide)propargylic Alcohols to Spiro[indene-benzosultam]s. Org Lett. 2015 Jan 16;17(2):242-5. PubMed PMID: 25541815.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Lewis acid catalyzed cascade reaction of 3-(2-benzenesulfonamide)propargylic alcohols to spiro[indene-benzosultam]s. AU - Sun,Lang, AU - Zhu,Yuanxun, AU - Wang,Jing, AU - Lu,Ping, AU - Wang,Yanguang, Y1 - 2014/12/26/ PY - 2014/12/27/entrez PY - 2014/12/30/pubmed PY - 2015/9/1/medline SP - 242 EP - 5 JF - Organic letters JO - Org Lett VL - 17 IS - 2 N2 - A highly efficient and convenient construction of the spiro[indene-benzosultam] skeleton from propargylic alcohols has been developed. The reaction proceeded in a Lewis acid catalyzed cascade process, including the trapping of allene carbocation with sulfonamide, electrophilic cyclization, and intramolecular Friedel-Crafts alkylation. In the presence of NIS or NBS, iodo/bromo-substituted spiro[indene-benzosultam]s could be prepared in excellent yields. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/25541815/Lewis_acid_catalyzed_cascade_reaction_of_3__2_benzenesulfonamide_propargylic_alcohols_to_spiro[indene_benzosultam]s_ DB - PRIME DP - Unbound Medicine ER -