Synthesis and use of benzyl tert-butyl iminodicarbonate, a versatile reagent for the preparation of amines

1988 ◽  
Vol 53 (11) ◽  
pp. 2778-2786 ◽  
Author(s):  
Leif Grehn ◽  
Ulf Ragnarsson
Keyword(s):  
Benzyl Alcohol ◽  
Sodium Salt ◽  
Title Compound ◽  
Protecting Groups ◽  
Efficient Synthesis ◽  
Tert Butyl ◽  
Mild Conditions ◽  
High Yields ◽  
Versatile Reagent

An efficient synthesis of benzyl tert-butyl iminodicarbonate (IV), starting from benzoyl isocyanate, is reported. Reaction of the isocyanate with benzyl alcohol gave benzyl N-benzoylcarbamate (II) which on exhaustive tert-butoxycarbonylation via the non-isolated triacyl amine III, after aminolysis, provided the title compound. The sodium salt V was alkylated with various halides under Gabriel conditions to give in high yields the corresponding benzyloxycarbonyl tert-butoxycarbonyl diprotected amines. Similarly, compound IV was alkylated with alcohols under Mitsunobu conditions to give some additional amines of this type, from which the protecting groups can be removed selectively under mild conditions.

Convenient and efficient synthesis of disubstituted piperazine derivatives by catalyst-free, atom-economical and tricomponent domino reactions

RSC Advances ◽  
2015 ◽  
Vol 5 (14) ◽  
pp. 10768-10772 ◽  
Author(s):  
Hong-Ru Dong ◽  
Zi-Bao Chen ◽  
Rong-Shan Li ◽  
Heng-Shan Dong ◽  
Zhi-Xiang Xie
Keyword(s):  
Free Atom ◽  
Domino Reactions ◽  
Efficient Synthesis ◽  
One Pot ◽  
Diversity Oriented Synthesis ◽  
Mild Conditions ◽  
Catalyst Free ◽  
Piperazine Derivatives ◽  
High Yields

One-pot, atom-economical, catalyst-free and tri-component domino reactions are applied to diversity-oriented synthesis (DOS) of disubstituted piperazine derivatives under mild conditions with moderate to high yields.

Monomeres [(Me3Si)2CH]2Al-Te-Al[CH(SiMe3)2]2 mit gewinkelter Al-Te-Al-Gruppe / Monomeric [(Me3Si)2CH]2Al-Te-Al[CH(SiMe3)2] 2 with a Bent Al-Te-Al Group

1994 ◽  
Vol 49 (7) ◽  
pp. 931-934 ◽  
Author(s):  
Werner Uhl ◽  
Uwe Schütz
Keyword(s):  
Solid State ◽  
Bond Length ◽  
Title Compound ◽  
Single Bond ◽  
Hindered Rotation ◽  
Coordination Numbers ◽  
Mild Conditions ◽  
High Yields

AbstractTetrakis[bis(trimethylsilyl)methyl]dialane(4) 1 with an Al-Al bond and Et3P+-Te- give under mild conditions the title compound R2Al-Te-AlR2 (R = CH(SiMe3)2) 2 in high yields. Due to the high steric shielding 2 is monomeric even in the solid state with an angled Al-Te-Al group (110.4°) and an Al-Te bond length of 254.9 pm as expected for a Al-T e single bond with the atoms in low coordination numbers. A hindered rotation of the bulky substituents is observed in solution probably caused by steric restrictions similar that in ana­logous compounds with Al-S-Al or Al-CH2-Al groups.

Coupling reaction of Aryl Halides Promoted by NiCl2/PPh3/Sm0

2002 ◽  
Vol 2002 (11) ◽  
pp. 562-563 ◽  
Author(s):  
Xingliang Zheng ◽  
Yongmin Zhang
Keyword(s):  
Functional Groups ◽  
Coupling Reaction ◽  
Aryl Halides ◽  
Efficient Synthesis ◽  
Mild Conditions ◽  
Coupling Reagent ◽  
High Yields

An efficient synthesis of biaryls from various aryl halides has been developed and investigated. The coupling reagent is a catalytic mixture of anhydrous NiCl2 and PPh3 in the presence of metallic samarium. The reaction occurs rapidly under mild conditions, tolerates a variety of functional groups with high yields.

3,5-Di-tert-butyl-1,2-benzoquinone Cleaves a CC-bond in Vicinal Aminobenzyl Alcohols

1994 ◽  
Vol 59 (1) ◽  
pp. 227-230 ◽  
Author(s):  
Václav Horák ◽  
Yonco Mermersky ◽  
Dalal B. Guirguis
Keyword(s):  
Bond Cleavage ◽  
Tert Butyl ◽  
Mild Conditions ◽  
High Yields

Two vicinal aminobenzyl alcohols, L-threo-1-(4-methylthiophenyl)-2-amino-1,3-propanediol (IIa) and 1-phenyl-2-amino-1,3-propanediol (IIb), underwent, under mild conditions, CC-bond cleavage with 3,5-di-tert-butyl-1,2-benzoquinone (I) producing in high yields 4-methylthiobenzaldehyde (Va) and benzaldehyde (Vb), respectively, and 2-hydroxymethyl-4,6-di-tert-butylbenzoxazole (VII). Ethanolamine (VIII) under identical conditions produced benzoxazole VII. The reported reaction is a second case in which quinone I mimics reactions of pyridoxal.

scholarly journals Convenient and Efficient Synthesis of Functionalized 2-Sulfenylindoles

Materials ◽  
2020 ◽  
Vol 13 (20) ◽  
pp. 4492
Author(s):  
Justyna Doroszuk ◽  
Mateusz Musiejuk ◽  
Bartosz Jędrzejewski ◽  
Juliusz Walczak ◽  
Dariusz Witt
Keyword(s):  
Efficient Synthesis ◽  
Mild Conditions ◽  
High Yields

A simple, efficient, and practical sulfenylation at the C2 position of N-tosylindoles under mild conditions was developed. The designed transformation is based on the reaction of N-tosylindoles with BuLi and S-alkyl, and S-aryl phosphorodithioates or thiotosylates to produce 2-sulfenylindoles in moderate to high yields. The presence of additional hydroxy, carboxy, or amino functionalities did not disturb the formation of products.

scholarly journals Simple and Efficient Synthesis of Allyl Sulfones through Cs2CO3-Mediated Radical Sulfonylation of Morita–Baylis–Hillman Adducts with Thiosulfonates

SynOpen ◽  
2021 ◽  
Vol 05 (01) ◽  
pp. 91-99
Author(s):  
Raju Jannapu Reddy ◽  
Angothu Shankar ◽  
Md. Waheed
Keyword(s):  
Efficient Synthesis ◽  
Mild Conditions ◽  
Highly Efficient ◽  
Plausible Mechanism ◽  
High Yields

AbstractA highly efficient and eco-friendly method has been developed for the synthesis of allyl sulfones using Morita–Baylis–Hillman (MBH) adducts and thiosulfonates under mild conditions. The Cs2CO3-promoted radical sulfonylation provided a series of allyl sulfones in good to high yields with high stereoselectivities. A wide variety of MBH bromides/acetates as well as thiosulfonates were tolerated and reliable in scaled-up synthesis. A plausible mechanism is proposed to rationalize the radical sulfonylation.

Versatile Synthesis of Functionalized Tetrahydroisoquinolines by Ring Transformation of 2H-Pyran-2-ones

2019 ◽  
Vol 72 (7) ◽  
pp. 524 ◽  
Author(s):  
Priyanka B. Kole ◽  
Fateh V. Singh
Keyword(s):  
Heterocyclic Compounds ◽  
Efficient Synthesis ◽  
Ring Transformation ◽  
Tert Butyl ◽  
High Yields

Functionalized tetrahydroisoquinolines are convenient precursors for the construction of numerous heterocyclic compounds of therapeutic importance. In this paper we have illustrated an efficient synthesis of highly substituted tetrahydroisoquinolines from 2H-pyran-2-ones via nucleophile-mediated ring transformation with tert-butyl-4-oxopiperidine-1-carboxylate followed by acid-mediated cleavage of the tert-butyloxycarbonyl group. The products were achieved smoothly in high yields with flexibility of various substituents.

scholarly journals An Efficient Greener Approach for N-acylation of Amines in Water Using Benzotriazole Chemistry

Molecules ◽  
2020 ◽  
Vol 25 (11) ◽  
pp. 2501 ◽  
Author(s):  
Tarek S. Ibrahim ◽  
Israa A. Seliem ◽  
Siva S. Panda ◽  
Amany M. M. Al-Mahmoudy ◽  
Zakaria K. M. Abdel-Samii ◽  
...  
Keyword(s):  
Amino Acid ◽  
Reaction Time ◽  
Microwave Irradiation ◽  
Room Temperature ◽  
Efficient Synthesis ◽  
Short Reaction Time ◽  
Mild Conditions ◽  
Drug Conjugates ◽  
Cost Efficient ◽  
High Yields

A straightforward, mild and cost-efficient synthesis of various arylamides in water was accomplished using versatile benzotriazole chemistry. Acylation of various amines was achieved in water at room temperature as well as under microwave irradiation. The developed protocol unfolds the synthesis of amino acid aryl amides, drug conjugates and benzimidazoles. The environmentally friendly synthesis, short reaction time, simple workup, high yields, mild conditions and free of racemization are the key advantages of this protocol.

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