e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

3, 6??diisopropyl??2??hydroxypyrazine and 3, 6??diisopropyl??2??pyrazinethiol as carriers of some alkoxycarbonyl groups

A Ohta, Y Inagawa, C Mitsugi

Index: Ohta, Akihiro; Inagawa, Yukiko; Mitsugi, Chie Journal of Heterocyclic Chemistry, 1985 , vol. 22, p. 1643 - 1646

Full Text: HTML

Citation Number: 9

Abstract

Abstract Some derivatives of benzyloxycarbonylated 3, 6-diisopropyl-2-hydroxypyrazine and 3, 6-diisopropyl-2-pyrazinethiol were prepared and shown to be the versatile benzyloxycarbonylation reagents for amines and amino acids. It was also ascertained that 3, 6-diisopropyl-2-hydroxypyrazine and 3, 6-diisopropyl-2-pyrazine-thiol serve effectively as carriers of the β, β, β,-trichloroethoxycarbonyl group.

2-Benzyloxycarbonyloxy-3,6-diisopropylpyrazine Structure

2-Benzyloxycarb...

Benzylamine Structure

~95%

(Phenylmethyl)-carbamic acid phenylmethyl ester Structure

(Phenylmethyl)-...

2(1H)-Pyrazinone,3,6-bis(1-methylethyl)-(9CI) Structure

2(1H)-Pyrazinon...

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Benzyl S-3,6-diisopropylpyrazin-2-ylthiolcarbonate Structure

Benzyl S-3,6-di...

Benzylamine Structure

~89%

(Phenylmethyl)-carbamic acid phenylmethyl ester Structure

(Phenylmethyl)-...

3,6-Diisopropyl-2-pyrazinethiol Structure

3,6-Diisopropyl...

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3,6-Diisopropyl-2-p-nitrobenzyloxycarbonyloxypyrazine Structure

3,6-Diisopropyl...

Benzylamine Structure

~89%

(4-nitrophenyl)methyl N-benzylcarbamate Structure

(4-nitrophenyl)...

2(1H)-Pyrazinone,3,6-bis(1-methylethyl)-(9CI) Structure

2(1H)-Pyrazinon...

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p-Nitrobenzyl S-3,6-Diisopropylpyrazin-2-ylthiolcarbonate Structure

p-Nitrobenzyl S...

Benzylamine Structure

~82%

(4-nitrophenyl)methyl N-benzylcarbamate Structure

(4-nitrophenyl)...

3,6-Diisopropyl-2-pyrazinethiol Structure

3,6-Diisopropyl...

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(4-Nitrophenyl)methanol Structure

(4-Nitrophenyl)...

~%

(4-nitrophenyl)methyl N-benzylcarbamate Structure

(4-nitrophenyl)...

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L-alanine Structure

2-Benzyloxycarbonyloxy-3,6-diisopropylpyrazine Structure

2-Benzyloxycarb...

~87%

N-Carbobenzyloxy-L-alanine Structure

N-Carbobenzylox...

2(1H)-Pyrazinone,3,6-bis(1-methylethyl)-(9CI) Structure

2(1H)-Pyrazinon...

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L-alanine Structure

Benzyl S-3,6-diisopropylpyrazin-2-ylthiolcarbonate Structure

Benzyl S-3,6-di...

~95%

N-Carbobenzyloxy-L-alanine Structure

N-Carbobenzylox...

3,6-Diisopropyl-2-pyrazinethiol Structure

3,6-Diisopropyl...

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L-alanine Structure

2-Benzyloxycarbonyloxy-3,6-diisopropylpyrazine Structure

2-Benzyloxycarb...

~0%

N-Carbobenzyloxy-L-alanine Structure

N-Carbobenzylox...

2(1H)-Pyrazinone,3,6-bis(1-methylethyl)-(9CI) Structure

2(1H)-Pyrazinon...

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L-alanine Structure

3,6-Diisopropyl-2-p-nitrobenzyloxycarbonyloxypyrazine Structure

3,6-Diisopropyl...

~0%

pnz-l-alanine Structure

2(1H)-Pyrazinone,3,6-bis(1-methylethyl)-(9CI) Structure

2(1H)-Pyrazinon...

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2-Benzyloxycarbonyloxy-3,6-diisopropylpyrazine Structure

2-Benzyloxycarb...

N-Methylbenzylamine Structure

N-Methylbenzylamine

~0%

2(1H)-Pyrazinone,3,6-bis(1-methylethyl)-(9CI) Structure

2(1H)-Pyrazinon...

N-benzyl-N-methylcarbamic acid benzyl ester Structure

N-benzyl-N-meth...

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3,6-Diisopropyl-2-p-nitrobenzyloxycarbonyloxypyrazine Structure

3,6-Diisopropyl...

N-Methylbenzylamine Structure

N-Methylbenzylamine

~0%

p-Nitrobenzyl Benzylmethylaminoformate Structure

p-Nitrobenzyl B...

2(1H)-Pyrazinone,3,6-bis(1-methylethyl)-(9CI) Structure

2(1H)-Pyrazinon...

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3,6-Diisopropyl-2-β,β,β-trichloroethoxycarbonyloxypyrazine Structure

3,6-Diisopropyl...

Benzylamine Structure

~0%

β,β,β-Trichloroethyl Benzylaminoformate Structure

β,β,β-Trichloro...

2(1H)-Pyrazinone,3,6-bis(1-methylethyl)-(9CI) Structure

2(1H)-Pyrazinon...

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2-Benzyloxycarbonyloxy-3,6-diisopropylpyrazine Structure

2-Benzyloxycarb...

L(-)-Tryptophan Structure

L(-)-Tryptophan

~0%

2(1H)-Pyrazinone,3,6-bis(1-methylethyl)-(9CI) Structure

2(1H)-Pyrazinon...

N-Cbz-L-Tryptophan Structure

N-Cbz-L-Tryptophan

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3,6-Diisopropyl-2-p-methylbenzyloxycarbonyloxypyrazine Structure

3,6-Diisopropyl...

N-Methylbenzylamine Structure

N-Methylbenzylamine

~0%

p-Methylbenzyl Benzylmethylaminoformate Structure

p-Methylbenzyl ...

2(1H)-Pyrazinone,3,6-bis(1-methylethyl)-(9CI) Structure

2(1H)-Pyrazinon...

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2-Benzyloxycarbonyloxy-3,6-diisopropylpyrazine Structure

2-Benzyloxycarb...

L(-)-Tryptophan Structure

L(-)-Tryptophan

~91%

2(1H)-Pyrazinone,3,6-bis(1-methylethyl)-(9CI) Structure

2(1H)-Pyrazinon...

N-Cbz-L-Tryptophan Structure

N-Cbz-L-Tryptophan

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Benzyl S-3,6-diisopropylpyrazin-2-ylthiolcarbonate Structure

Benzyl S-3,6-di...

L(-)-Tryptophan Structure

L(-)-Tryptophan

~92%

3,6-Diisopropyl-2-pyrazinethiol Structure

3,6-Diisopropyl...

N-Cbz-L-Tryptophan Structure

N-Cbz-L-Tryptophan

Learn More

L-alanine Structure

3,6-Diisopropyl-2-p-methylbenzyloxycarbonyloxypyrazine Structure

3,6-Diisopropyl...

~0%

L-N(p-Methylbenzyloxycarbonyl)alanine Structure

L-N(p-Methylben...

2(1H)-Pyrazinone,3,6-bis(1-methylethyl)-(9CI) Structure

2(1H)-Pyrazinon...

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3,6-Diisopropyl-2-β,β,β-trichloroethoxycarbonyloxypyrazine Structure

3,6-Diisopropyl...

N-Methylbenzylamine Structure

N-Methylbenzylamine

~0%

β,β,β-Trichloroethyl Benzylmethylaminoformate Structure

β,β,β-Trichloro...

2(1H)-Pyrazinone,3,6-bis(1-methylethyl)-(9CI) Structure

2(1H)-Pyrazinon...

Learn More

2-Benzyloxycarbonyloxy-3,6-diisopropylpyrazine Structure

2-Benzyloxycarb...

Benzylamine Structure

~0%

(Phenylmethyl)-carbamic acid phenylmethyl ester Structure

(Phenylmethyl)-...

2(1H)-Pyrazinone,3,6-bis(1-methylethyl)-(9CI) Structure

2(1H)-Pyrazinon...

Learn More

3,6-Diisopropyl-2-p-methylbenzyloxycarbonyloxypyrazine Structure

3,6-Diisopropyl...

Benzylamine Structure

~0%

benzylcarbamic acid 4-methylbenzyl ester Structure

benzylcarbamic ...

2(1H)-Pyrazinone,3,6-bis(1-methylethyl)-(9CI) Structure

2(1H)-Pyrazinon...

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3,6-Diisopropyl-2-p-nitrobenzyloxycarbonyloxypyrazine Structure

3,6-Diisopropyl...

Benzylamine Structure

~0%

(4-nitrophenyl)methyl N-benzylcarbamate Structure

(4-nitrophenyl)...

2(1H)-Pyrazinone,3,6-bis(1-methylethyl)-(9CI) Structure

2(1H)-Pyrazinon...

Learn More

3,6-Diisopropyl-2-p-methylbenzyloxycarbonyloxypyrazine Structure

3,6-Diisopropyl...

L(-)-Tryptophan Structure

L(-)-Tryptophan

~0%

L-Nα-(p-Methylbenzyloxycarbonyl)tryptophan Structure

L-Nα-(p-Methylb...

2(1H)-Pyrazinone,3,6-bis(1-methylethyl)-(9CI) Structure

2(1H)-Pyrazinon...

Learn More

3,6-Diisopropyl-2-p-nitrobenzyloxycarbonyloxypyrazine Structure

3,6-Diisopropyl...

L(-)-Tryptophan Structure

L(-)-Tryptophan

~0%

Nα-(4-nitro-benzyloxycarbonyl)-DL-tryptophan Structure

Nα-(4-nitro-ben...

2(1H)-Pyrazinone,3,6-bis(1-methylethyl)-(9CI) Structure

2(1H)-Pyrazinon...

Learn More

L-alanine Structure

3,6-Diisopropyl-2-p-nitrobenzyloxycarbonyloxypyrazine Structure

3,6-Diisopropyl...

~84%

pnz-l-alanine Structure

2(1H)-Pyrazinone,3,6-bis(1-methylethyl)-(9CI) Structure

2(1H)-Pyrazinon...

Learn More

L-alanine Structure

p-Nitrobenzyl S-3,6-Diisopropylpyrazin-2-ylthiolcarbonate Structure

p-Nitrobenzyl S...

~88%

pnz-l-alanine Structure

3,6-Diisopropyl-2-pyrazinethiol Structure

3,6-Diisopropyl...

Learn More

(4-Nitrophenyl)methanol Structure

(4-Nitrophenyl)...

~%

pnz-l-alanine Structure

Learn More

Reductive cleavage of N O bonds in hydroxylamine and hydrox...

[Keck, Gary E.; McHardy, Stanton F.; Wager, Travis T. Tetrahedron Letters, 1995 , vol. 36, # 41 p. 7419 - 7422]

A facile deprotection of secondary acetamides

[Koenig, Stefan G.; Vandenbossche, Charles P.; Zhao, Hang; Mousaw, Patrick; Singh, Surendra P.; Bakale, Roger P. Organic Letters, 2009 , vol. 11, # 2 p. 433 - 436]

Reductive N-alkylation of amides, carbamates and ureas

[Dube, Daniel; Scholte, Andrew A. Tetrahedron Letters, 1999 , vol. 40, # 12 p. 2295 - 2298]

Synthetic and structural studies on 1, 2, 4-dithiazolidine-3...

[Wood, Mark E.; Cane-Honeysett, Daniel J.; Dowle, Michael D.; Coles, Simon J.; Hursthouse, Michael B. Organic and Biomolecular Chemistry, 2003 , vol. 1, # 17 p. 3015 - 3023]

Alkyl 1-chloroalkyl carbonates: Reagents for the synthesis o...

[Barcelo, Gerard; Senet, Jean-Pierre; Sennyey, Gerard; Bensoam, Jean; Loffet, Albert Synthesis, 1986 , # 8 p. 627 - 632]