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Keywords:

  • alcohols;
  • alkylation;
  • ketones;
  • nucleophilic addition;
  • platinum

Abstract

N-Methyl indole reacts with but-2-yn-1-ol in the presence of PtCl2 in MeOH giving indole derivatives having a substituted 3-oxobutyl group at the 3-position in good yield. Under the reaction conditions, various substituted indoles and substituted propargyl alcohols are successfully involved in the reaction giving the corresponding addition products in good to moderate yields. The catalytic reaction can be further extended to N-phenyl pyrrole. In the present multi-step reaction, PtCl2 likely plays dual roles: as the catalyst for the rearrangement of propargyl alcohols to the corresponding alkenyl ketones and as the catalyst for the addition of indoles to the alkenyl ketones. Experimental evidence is provided to support the proposed mechanism.

Featured Compounds

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  1. 1 - 52
Compound 1a
Molecular Weight:131.1745
Molecular Formula:C9H9N
InChIKey:BLRHMMGNCXNXJL-UHFFFAOYSA-N
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Compound 2a
Molecular Weight:70.0898
Molecular Formula:C4H6O
InChIKey:NEEDEQSZOUAJMU-UHFFFAOYSA-N
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Compound 1i
Molecular Weight:117.1479
Molecular Formula:C8H7N
InChIKey:SIKJAQJRHWYJAI-UHFFFAOYSA-N
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Compound 1j
Molecular Weight:143.1852
Molecular Formula:C10H9N
InChIKey:GEZGAZKEOUKLBR-UHFFFAOYSA-N
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Compound 3a
Molecular Weight:201.2643
Molecular Formula:C13H15NO
InChIKey:IAHRGKFNNBJULE-UHFFFAOYSA-N
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Compound 3
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 1b
Molecular Weight:161.2004
Molecular Formula:C10H11NO
InChIKey:HQNPKVBTBJUMTR-UHFFFAOYSA-N
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Compound 3b
Molecular Weight:231.2903
Molecular Formula:C14H17NO2
InChIKey:UDFKHFCJJTZDNN-UHFFFAOYSA-N
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Compound 1c
Molecular Weight:210.071
Molecular Formula:C9H8BrN
InChIKey:SBOITLSQLQGSLO-UHFFFAOYSA-N
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Compound 1d
Molecular Weight:257.071
Molecular Formula:C9H8IN
InChIKey:DYHWMNMFESGBJZ-UHFFFAOYSA-N
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Compound 1e
Molecular Weight:176.172
Molecular Formula:C9H8N2O2
InChIKey:PXBQSCHRKSBGKV-UHFFFAOYSA-N
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Compound 3d
Molecular Weight:327.1608
Molecular Formula:C13H14INO
InChIKey:MEIUICWHIIGHGI-UHFFFAOYSA-N
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Compound 3e
Molecular Weight:246.2619
Molecular Formula:C13H14N2O3
InChIKey:JCJVIQAVPPVBAF-UHFFFAOYSA-N
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Compound 3f
Molecular Weight:231.2903
Molecular Formula:C14H17NO2
InChIKey:RVGIQZHHDCFHCZ-UHFFFAOYSA-N
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Compound 1f
Molecular Weight:161.2004
Molecular Formula:C10H11NO
InChIKey:VTJXLVGZNOINAD-UHFFFAOYSA-N
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Compound 1g
Molecular Weight:161.2004
Molecular Formula:C10H11NO
InChIKey:XOAZJKTUIFSUGD-UHFFFAOYSA-N
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Compound 3g
Molecular Weight:231.2903
Molecular Formula:C14H17NO2
InChIKey:VSGKHPDQKHZOGI-UHFFFAOYSA-N
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Compound 1h
Molecular Weight:145.201
Molecular Formula:C10H11N
InChIKey:BJMUOUXGBFNLSN-UHFFFAOYSA-N
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Compound 3h
Molecular Weight:215.2909
Molecular Formula:C14H17NO
InChIKey:ZEISIUHQYOXYTM-UHFFFAOYSA-N
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Compound 3c
Molecular Weight:280.16
Molecular Formula:C13H14BrNO
InChIKey:CYTWJULOYRCJGG-UHFFFAOYSA-N
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Compound 3i
Molecular Weight:187.2377
Molecular Formula:C12H13NO
InChIKey:ZJCUUXGLZWBCIL-UHFFFAOYSA-N
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Compound 2b
Molecular Weight:84.1164
Molecular Formula:C5H8O
InChIKey:WLPYSOCRPHTIDZ-UHFFFAOYSA-N
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Compound 2c
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:BTDWSZJDLLLTMI-UHFFFAOYSA-N
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Compound 2d
Molecular Weight:132.1592
Molecular Formula:C9H8O
InChIKey:NITUNGCLDSFVDL-UHFFFAOYSA-N
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Compound 2e
Molecular Weight:138.187
Molecular Formula:C7H6OS
InChIKey:SVYGRAAJWLKOCZ-UHFFFAOYSA-N
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Compound 2f
Molecular Weight:146.1858
Molecular Formula:C10H10O
InChIKey:JYOZFNMFSVAZAW-UHFFFAOYSA-N
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Compound 2g
Molecular Weight:174.239
Molecular Formula:C12H14O
InChIKey:KRXFLLINIVIGNG-UHFFFAOYSA-N
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Compound 3j
Molecular Weight:215.2909
Molecular Formula:C14H17NO
InChIKey:XXBWDHPHAXWMEX-UHFFFAOYSA-N
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Compound 3k
Molecular Weight:215.2909
Molecular Formula:C14H17NO
InChIKey:XXBWDHPHAXWMEX-UHFFFAOYSA-N
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Compound 3l
Molecular Weight:263.3337
Molecular Formula:C18H17NO
InChIKey:KCWBVEFKNWMSRJ-UHFFFAOYSA-N
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Compound 3m
Molecular Weight:269.361
Molecular Formula:C16H15NOS
InChIKey:KVJMVIHGABHEEO-UHFFFAOYSA-N
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Compound 3n
Molecular Weight:277.3603
Molecular Formula:C19H19NO
InChIKey:AJOZGOGEOMGFPK-UHFFFAOYSA-N
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Compound 3o
Molecular Weight:305.4134
Molecular Formula:C21H23NO
InChIKey:XCIRZWPAUAQBNN-UHFFFAOYSA-N
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Compound 2
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 3p
Molecular Weight:213.275
Molecular Formula:C14H15NO
InChIKey:BYXIFNCITOJRPM-UHFFFAOYSA-N
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Compound 3q
Molecular Weight:281.372
Molecular Formula:C17H15NOS
InChIKey:VQRJXRWUXNICDF-UHFFFAOYSA-N
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Compound 4a
Molecular Weight:164.2011
Molecular Formula:C10H12O2
InChIKey:MZBFZHPHBGPWDT-UHFFFAOYSA-N
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Compound 4c
Molecular Weight:234.334
Molecular Formula:C15H22O2
InChIKey:LWQQVNCDCAWNJV-UHFFFAOYSA-N
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Compound 4d
Molecular Weight:192.2542
Molecular Formula:C12H16O2
InChIKey:XCOLZHTYXZKPHW-UHFFFAOYSA-N
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Compound 4e
Molecular Weight:232.3181
Molecular Formula:C15H20O2
InChIKey:HCXZRADYWKPVJK-UHFFFAOYSA-N
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Compound 4f
Molecular Weight:132.1592
Molecular Formula:C9H8O
InChIKey:KUIZKZHDMPERHR-UHFFFAOYSA-N
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Compound 4g
Molecular Weight:186.2912
Molecular Formula:C11H22O2
InChIKey:PNGHOCLKZYTHIX-UHFFFAOYSA-N
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Compound 4b
Molecular Weight:178.2277
Molecular Formula:C11H14O2
InChIKey:AUOLHXKGWUNYJA-UHFFFAOYSA-N
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Compound 4
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 2h
Molecular Weight:174.239
Molecular Formula:C12H14O
InChIKey:MTBIBEIZKLZPIM-UHFFFAOYSA-N
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Compound 5b
Molecular Weight:202.2921
Molecular Formula:C14H18O
InChIKey:LJXMKVSUYXCRED-UHFFFAOYSA-N
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Compound 9
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 5a
Molecular Weight:188.2655
Molecular Formula:C13H16O
InChIKey:UHSDDDXBOGNSRJ-UHFFFAOYSA-N
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Compound 12
Molecular Weight:70.0898
Molecular Formula:C4H6O
InChIKey:RRWJXAJEGRDMQH-UHFFFAOYSA-N
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Compound 3r
Molecular Weight:187.2377
Molecular Formula:C12H13NO
InChIKey:WAOFJJFRSUTEGC-UHFFFAOYSA-N
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Compound 9a
Molecular Weight:84.1164
Molecular Formula:C5H8O
InChIKey:Not Available
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Compound 9b
Molecular Weight:84.1164
Molecular Formula:C5H8O
InChIKey:Not Available
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  1. 1 - 52