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Pd-catalyzed cascade cyclization by intramolecular Heck insertion of an allene-allylic amination sequence: application to the synthesis of 3,4-fused tricyclic indoles.
Org Lett. 2015 Jun 05; 17(11):2622-5.OL

Abstract

A novel Pd-catalyzed cascade cyclization by intramolecular Heck insertion of an allene-allylic amination sequence was developed. Allenes tethered to ortho-iodoaniline derivatives at the meta-position were reacted with 5-10 mol % of Pd catalyst and 4 equiv of K2CO3 in DMSO at 90 °C, producing 3,4-fused tricyclic 3-alkylidene indoline derivatives in moderate to excellent yield. The reaction products were divergently transformed into three types of 3,4-fused tricyclic indole derivatives, successfully demonstrating the versatile properties of the reaction products.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Nakano S
Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuo-ku, Chiba 260-8675, Japan.
Inoue N
Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuo-ku, Chiba 260-8675, Japan.
Hamada Y
Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuo-ku, Chiba 260-8675, Japan.
Nemoto T
Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuo-ku, Chiba 260-8675, Japan.

MeSH

AminationCatalysisCyclizationIndolesMolecular StructureOrganometallic CompoundsPalladium

Pub Type(s)

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

Language

eng

PubMed ID

25990671

Citation

Nakano, Shun-ichi, et al. "Pd-catalyzed Cascade Cyclization By Intramolecular Heck Insertion of an Allene-allylic Amination Sequence: Application to the Synthesis of 3,4-fused Tricyclic Indoles." Organic Letters, vol. 17, no. 11, 2015, pp. 2622-5.
Nakano S, Inoue N, Hamada Y, et al. Pd-catalyzed cascade cyclization by intramolecular Heck insertion of an allene-allylic amination sequence: application to the synthesis of 3,4-fused tricyclic indoles. Org Lett. 2015;17(11):2622-5.
Nakano, S., Inoue, N., Hamada, Y., & Nemoto, T. (2015). Pd-catalyzed cascade cyclization by intramolecular Heck insertion of an allene-allylic amination sequence: application to the synthesis of 3,4-fused tricyclic indoles. Organic Letters, 17(11), 2622-5. https://doi.org/10.1021/acs.orglett.5b00973
Nakano S, et al. Pd-catalyzed Cascade Cyclization By Intramolecular Heck Insertion of an Allene-allylic Amination Sequence: Application to the Synthesis of 3,4-fused Tricyclic Indoles. Org Lett. 2015 Jun 5;17(11):2622-5. PubMed PMID: 25990671.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Pd-catalyzed cascade cyclization by intramolecular Heck insertion of an allene-allylic amination sequence: application to the synthesis of 3,4-fused tricyclic indoles. AU - Nakano,Shun-ichi, AU - Inoue,Naoya, AU - Hamada,Yasumasa, AU - Nemoto,Tetsuhiro, Y1 - 2015/05/20/ PY - 2015/5/21/entrez PY - 2015/5/21/pubmed PY - 2015/10/10/medline SP - 2622 EP - 5 JF - Organic letters JO - Org Lett VL - 17 IS - 11 N2 - A novel Pd-catalyzed cascade cyclization by intramolecular Heck insertion of an allene-allylic amination sequence was developed. Allenes tethered to ortho-iodoaniline derivatives at the meta-position were reacted with 5-10 mol % of Pd catalyst and 4 equiv of K2CO3 in DMSO at 90 °C, producing 3,4-fused tricyclic 3-alkylidene indoline derivatives in moderate to excellent yield. The reaction products were divergently transformed into three types of 3,4-fused tricyclic indole derivatives, successfully demonstrating the versatile properties of the reaction products. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/25990671/Pd_catalyzed_cascade_cyclization_by_intramolecular_Heck_insertion_of_an_allene_allylic_amination_sequence:_application_to_the_synthesis_of_34_fused_tricyclic_indoles_ DB - PRIME DP - Unbound Medicine ER -