Iodotrimethylsilane: A mild and efficient reagent for the reduction of azides to amines

Kamal, Ähmed; Rao, N. Venkateswara; Laxman, E.

doi:10.1016/s0040-4039(97)01628-6

Cited by 63 publications

(30 citation statements)

References 15 publications

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“…Bu 3 SnH is also used as reducing agent, sometimes with Ni(II) catalysis,486, 487 although a radical mechanism is assumed here 486. Aliphatic, aromatic, and benzoyl azides can be reduced to the corresponding amines or amides by the action of trimethylchlorosilane 488. The direct conversion of organazides into Boc‐protected amines,465, 489 which provides elegant access to orthogonally protected diamines, is very attractive.…”

Section: Reactions Of Organic Azidesmentioning

confidence: 99%

Organic Azides: An Exploding Diversity of a Unique Class of Compounds

et al. 2005

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Since the discovery of organic azides by Peter Griess more than 140 years ago, numerous syntheses of these energy-rich molecules have been developed. In more recent times in particular, completely new perspectives have been developed for their use in peptide chemistry, combinatorial chemistry, and heterocyclic synthesis. Organic azides have assumed an important position at the interface between chemistry, biology, medicine, and materials science. In this Review, the fundamental characteristics of azide chemistry and current developments are presented. The focus will be placed on cycloadditions (Huisgen reaction), aza ylide chemistry, and the synthesis of heterocycles. Further reactions such as the aza-Wittig reaction, the Sundberg rearrangement, the Staudinger ligation, the Boyer and Boyer-Aubé rearrangements, the Curtius rearrangement, the Schmidt rearrangement, and the Hemetsberger rearrangement bear witness to the versatility of modern azide chemistry.

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Section: Reactions Of Organic Azidesmentioning

confidence: 99%

Organic Azides: An Exploding Diversity of a Unique Class of Compounds

et al. 2005

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“…Furthermore, the MALDI-TOF MS spectrum in Figure 5A indicates that the condensation of compounds 6 and 9 successfully proceeded to give a compound 10 (m/z There are some methods (Ranu et al 1994;Kamal et al 1997) to reduce the azide group into an amino group. The simple method using palladium carbon under hydrogen atmosphere was adopted in this reduction, intending to apply the method to the CTA derivative.…”

Section: Synthesis Of Cellobiosylamine Derivativementioning

confidence: 99%

Synthesis of diblock copolymers with cellulose derivatives. 1. Model study with azidoalkyl carboxylic acid and cellobiosylamine derivative

Kamitakahara

Nakatsubo

2005

Cellulose

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The basic strategy to make a well-defined A-block-B type cellulose derivative consisting of cellulose and a hydrophobic part was established. The model experiments using cellobiose derivatives play an important role in an actual synthesis of A-block-B type copolymer consisting of cellulose and a hydrophobic part with well-controlled length. A new hydrophobic building block, 15-azidopentadecanoyl chloride, was converted from a commercially available15-hydroxypentadecanoic acid. The novel hydrophobic linker, 15-azidopentadecanoyl chloride, was twice introduced into the reducing end of the cellobiosylamine derivative. The structures of the model compounds for A-block-B type copolymer consisting of sugar and non-sugar blocks were characterized by use of nuclear magnetic resonance (NMR) spectroscopy and Matrix Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometry (MALDI-TOF MS).

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“…Trimethylsilyli odide (TMSI) [26] generated in situ from trimethylsilylc hloride (TMSCl) and NaI in CH 3 CN is ap owerful reagent to reduce azides to amines, and has been adopted in the synthesis of solasodine, [16,27] the aglycone of solamargine. With glycoside 2 secured, formation of oxaazaspirodecane wasc onducted by treating 2 with TMSI (2.0 equiv., Scheme 2).…”

Section: Introductionmentioning

confidence: 99%

Convergent Synthesis of Solamargine and Analogues Thereof: Structural Revision of 16‐epi‐Solamargine and Cytotoxic Evaluation

et al. 2015

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An effective and stereoselective protocol for convergent synthesis of solamargine, ar epresentative of spirosolane-type glycoalkaloids, is reported. HB(C 6 F 5 ) 4 -catalyzed coupling of 26-azido-pseudodiosgenin with chacotriosyl trichloroacetimidate as the key step for synthesis of solamargine proceeded in high yield andw ith excellent stereoselectivity.T hree analogues of solamarginew ere synthesized by the method. Protonation of the nitrogen atom by deuterium chloride had as ignificant influenceo nt he 1 HNMR spectrum of solamargine. On the basis of theser esults, the structure of 16-epi-solamargine was revisedt os olamargine hydrochloride. The cytotoxicity of solamarginet ogether with its analogues against cancer cell lines was evaluated.

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Iodotrimethylsilane: A mild and efficient reagent for the reduction of azides to amines

Cited by 63 publications

References 15 publications

Organic Azides: An Exploding Diversity of a Unique Class of Compounds

Organic Azides: An Exploding Diversity of a Unique Class of Compounds

Synthesis of diblock copolymers with cellulose derivatives. 1. Model study with azidoalkyl carboxylic acid and cellobiosylamine derivative

Convergent Synthesis of Solamargine and Analogues Thereof: Structural Revision of 16‐epi‐Solamargine and Cytotoxic Evaluation

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