Access to Indole-Fused Benzannulated Medium-Sized Rings through a Gold(I)-Catalyzed Cascade Cyclization of Azido-Alkynes
Because benzannulated and indole-fused medium-sized rings are found in many bioactive compounds, combining these fragments might lead to unexplored areas of biologically relevant and uncovered chemical space. Herein is shown that α-imino gold carbene chem
Greiner, Luca C.,Inuki, Shinsuke,Arichi, Norihito,Oishi, Shinya,Suzuki, Rikito,Iwai, Tomohiro,Sawamura, Masaya,Hashmi, A. Stephen K.,Ohno, Hiroaki
p. 12992 - 12997
(2021/07/20)
An environmentally friendly protocol for oxidative halocyclization of tryptamine and tryptophol derivatives
An environmentally friendly and efficient protocol (KX/oxone) for oxidative halocyclization of tryptamine/tryptophol derivatives was developed and demonstrated with 28 examples and concise total synthesis of cyclotryptamine alkaloid protubonines A and B. The distinct advantage of this protocol over all previous methods is that no organic byproduct is generated from a halogenating agent or oxidant, thus greatly reducing the environmental impact of halocyclization and facilitating the post-reaction purification.
Xu, Jun,Tong, Rongbiao
p. 2952 - 2956
(2017/07/24)
[TPA][Pro] ionic liquid as efficient reaction medium for N-tert-Boc protection of amines
A facile and efficient N-tert-Boc protection of amines is described by the reaction of various primary, secondary, benzylic and aryl amines with di-tert-butyl dicarbonate in the ionic liquid [TPA][Pro] at room temperature. All the N-tert-butylcarbamates are afforded in excellent yields. A catalyst-free method was developed and the ionic liquid [TPA][Pro] can be recovered and reused for several times without loss of its activity.
Vijaya Durga,Rambabu,Srinivasa Reddy,Hari Babu
p. 1313 - 1316
(2017/05/02)
Catalytic asymmetric hydrogenation of indoles using a rhodium complex with a chiral bisphosphine ligand PhTRAP
Highly enantioselective hydrogenation of N-protected indoles was successfully developed by use of the rhodium catalyst generated in situ from [Rh(nbd)2]SbF6 and the chiral bisphosphine PhTRAP, which can form a trans-chelate complex with a transition metal atom. The PhTRAP-rhodium catalyst required a base (e.g., Cs2CO3) for the achievement of high enantioselectivity. Various 2-substituted N-acetylindoles were converted into the corresponding chiral indolines with up to 95% ee. The hydrogenations of 3-substituted N-tosylindoles yielded indolines possessing a stereogenic center at the 3-position with high enantiomeric excesses (up to 98% ee).
Facile N-tert-butoxycarbonylation of amines using La(NO3)3·6H2O as a mild and efficient catalyst under solvent-free conditions
Facile N-tert-butoxycarbonylation of amines is described by the treatment of various primary, secondary, benzylic and aryl amines with di-tert-butyl dicarbonate in the presence of catalytic amounts of La(NO3)3·6H2O under solvent-free conditions at room temperature to afford N-tert-butylcarbamates in excellent yields.
Suryakiran,Prabhakar,Reddy, T. Srikanth,Rajesh,Venkateswarlu
p. 8039 - 8042
(2007/10/03)
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