Matches in SemOpenAlex for { <https://semopenalex.org/work/W2058173832> ?p ?o ?g. }
- W2058173832 endingPage "8293" @default.
- W2058173832 startingPage "8285" @default.
- W2058173832 abstract "PtCl2 effectively catalyzes the multistep reaction of N-methyl indole (1 a) with pent-3-yn-1-ol (2 a) in THF at room temperature for 2 h to give indole derivative 3 a, which contains a five-membered cyclic ether group at C3 in 93% yield. Under similar reaction conditions, various substituted N-methyl indoles 1 b-h and indole (1 i) reacted efficiently with 2 a to afford the corresponding indole derivatives 3 b-h and 3 i in 48-91 and 72% yields. The results showed that N-methyl indoles with electron-donating substituents were more reactive affording higher product yields than those with electron-withdrawing groups. Likewise, various substituted but-3-yn-1-ols 2 b-e and other longer chain alkynyl alcohols 2 f-i also underwent a cyclization-addition reaction with N-methyl indole (1 a) to provide the corresponding cyclization-addition products 3 j-m and 3 a, 3 j, and 3 n-o in good to excellent yields. The present platinum-catalyzed cyclization-addition reaction can be further extended into N-methyl pyrrole. Mechanistically, the catalytic reaction proceeds by an intramolecular hydroalkoxylation of alkynyl alcohol to afford cyclic enol ether followed by the addition of the C--H bond of indole to the unsaturated moiety of cyclic enol ether providing the final product. Experimental evidence to support this proposed mechanism is provided." @default.
- W2058173832 created "2016-06-24" @default.
- W2058173832 creator A5007286739 @default.
- W2058173832 creator A5039710142 @default.
- W2058173832 creator A5069900066 @default.
- W2058173832 date "2007-09-25" @default.
- W2058173832 modified "2023-10-17" @default.
- W2058173832 title "Platinum-Catalyzed Multistep Reactions of Indoles with Alkynyl Alcohols" @default.
- W2058173832 cites W1972915646 @default.
- W2058173832 cites W1984115091 @default.
- W2058173832 cites W1992044814 @default.
- W2058173832 cites W1993403330 @default.
- W2058173832 cites W1996565721 @default.
- W2058173832 cites W1996869414 @default.
- W2058173832 cites W1998519155 @default.
- W2058173832 cites W2007416709 @default.
- W2058173832 cites W2010823595 @default.
- W2058173832 cites W2012265683 @default.
- W2058173832 cites W2016896228 @default.
- W2058173832 cites W2021846814 @default.
- W2058173832 cites W2025474947 @default.
- W2058173832 cites W2026895094 @default.
- W2058173832 cites W2037668530 @default.
- W2058173832 cites W2038607053 @default.
- W2058173832 cites W2042981847 @default.
- W2058173832 cites W2049069355 @default.
- W2058173832 cites W2049078107 @default.
- W2058173832 cites W2053520826 @default.
- W2058173832 cites W2060850694 @default.
- W2058173832 cites W2065510965 @default.
- W2058173832 cites W2073320300 @default.
- W2058173832 cites W2073435057 @default.
- W2058173832 cites W2075622879 @default.
- W2058173832 cites W2079903532 @default.
- W2058173832 cites W2080307346 @default.
- W2058173832 cites W2090569940 @default.
- W2058173832 cites W2090603266 @default.
- W2058173832 cites W2090868139 @default.
- W2058173832 cites W2091674812 @default.
- W2058173832 cites W2099674459 @default.
- W2058173832 cites W2102987254 @default.
- W2058173832 cites W2107181958 @default.
- W2058173832 cites W2110498029 @default.
- W2058173832 cites W2113087320 @default.
- W2058173832 cites W2113658180 @default.
- W2058173832 cites W2116906478 @default.
- W2058173832 cites W2126318985 @default.
- W2058173832 cites W2128147343 @default.
- W2058173832 cites W2134554187 @default.
- W2058173832 cites W2137792304 @default.
- W2058173832 cites W2144234884 @default.
- W2058173832 cites W2146451905 @default.
- W2058173832 cites W2147754196 @default.
- W2058173832 cites W2155619181 @default.
- W2058173832 cites W2162832633 @default.
- W2058173832 cites W2165157068 @default.
- W2058173832 cites W2166745737 @default.
- W2058173832 cites W2167148893 @default.
- W2058173832 cites W2167985748 @default.
- W2058173832 cites W2174189895 @default.
- W2058173832 cites W2175728713 @default.
- W2058173832 cites W2949292047 @default.
- W2058173832 cites W2949318951 @default.
- W2058173832 cites W2949790529 @default.
- W2058173832 cites W2949827563 @default.
- W2058173832 cites W2950033905 @default.
- W2058173832 cites W2950242998 @default.
- W2058173832 cites W2950290205 @default.
- W2058173832 cites W2950321589 @default.
- W2058173832 cites W2950401814 @default.
- W2058173832 cites W2950588986 @default.
- W2058173832 cites W2950707828 @default.
- W2058173832 cites W2950849042 @default.
- W2058173832 cites W2950937783 @default.
- W2058173832 cites W2951172880 @default.
- W2058173832 cites W2951221241 @default.
- W2058173832 cites W2951317440 @default.
- W2058173832 cites W2951470196 @default.
- W2058173832 cites W2951493441 @default.
- W2058173832 cites W2951519834 @default.
- W2058173832 cites W2951689228 @default.
- W2058173832 cites W2952414062 @default.
- W2058173832 cites W2952694920 @default.
- W2058173832 cites W2953307993 @default.
- W2058173832 cites W4231946512 @default.
- W2058173832 cites W4247851196 @default.
- W2058173832 cites W4377077185 @default.
- W2058173832 doi "https://doi.org/10.1002/chem.200700589" @default.
- W2058173832 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/17721891" @default.
- W2058173832 hasPublicationYear "2007" @default.
- W2058173832 type Work @default.
- W2058173832 sameAs 2058173832 @default.
- W2058173832 citedByCount "84" @default.
- W2058173832 countsByYear W20581738322012 @default.
- W2058173832 countsByYear W20581738322013 @default.
- W2058173832 countsByYear W20581738322014 @default.
- W2058173832 countsByYear W20581738322015 @default.
- W2058173832 countsByYear W20581738322016 @default.