Activated N-nitrosocarbamates for regioselective synthesis of N-nitrosoureas

…, J Oiry, JL Imbach, F Winternitz

Index: Martinez, Jean; Oiry, Joel; Imbach, Jean Louis; Winternitz, Francois Journal of Medicinal Chemistry, 1982 , vol. 25, # 2 p. 178 - 182

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Citation Number: 63

Abstract

A practical and convenient method for synthesizing antitumor compounds, N-alkyl-N- nitrosoureas, regioselectively nitrosated on the nitrogen atom bearing the alkyl group is proposed. N-Alkyl-N-nitrosocarbamates are interesting intermediates in these syntheses and yield, by reaction with amino compounds, the regioselectively nitrosated N-alkyl-N- nitrosoureas. As an interesting example, N, N'-bis [(2-chloroethyl) nitrosocarbamoyl] ...

 Related Synthetic Route
Methylisocyanate 1 x 500mg neat Structure

624-83-9

Methylisocyanat...

2,4,5-Trichlorophenol Structure

95-95-4

2,4,5-Trichloro...

~85%

Phenol,2,4,5-trichloro-, 1-(N-methylcarbamate) Structure

3942-57-2

Phenol,2,4,5-tr...

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Carbamic acid, (2-chloroethyl)-, 2,4,5-trichlorophenyl ester Structure

80354-46-7

Carbamic acid, ...

~94%

(2,4,5-trichlorophenyl) N-(2-chloroethyl)-N-nitroso-carbamate Structure

80354-51-4

(2,4,5-trichlor...

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1-Chloro-2-isocyanatoethane Structure

1943-83-5

1-Chloro-2-isoc...

2,4,5-Trichlorophenol Structure

95-95-4

2,4,5-Trichloro...

~81%

Carbamic acid, (2-chloroethyl)-, 2,4,5-trichlorophenyl ester Structure

80354-46-7

Carbamic acid, ...

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1-[(Methylcarbamoyl)oxy]-2,5-pyrrolidinedione Structure

18342-66-0

1-[(Methylcarba...

~98%

(2,5-dioxopyrrolidin-1-yl) N-methyl-N-nitrosocarbamate Structure

80354-48-9

(2,5-dioxopyrro...

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N-Hydroxysuccinimide Structure

6066-82-6

N-Hydroxysuccinimide

Methylisocyanate 1 x 500mg neat Structure

624-83-9

Methylisocyanat...

~80%

1-[(Methylcarbamoyl)oxy]-2,5-pyrrolidinedione Structure

18342-66-0

1-[(Methylcarba...

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(2,4,5-trichlorophenyl) N-(2-chloroethyl)-N-nitroso-carbamate Structure

80354-51-4

(2,4,5-trichlor...

Cystamine dihydrochloride Structure

56-17-7

Cystamine dihyd...

~73%

1-(2-chloroethyl)-3-[2-[2-[(2-chloroethyl-nitroso-carbamoyl)amino]ethy ldisulfanyl]ethyl]-1-nitroso-urea Structure

77469-44-4

1-(2-chloroethy...

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Cystamine dihydrochloride Structure

56-17-7

Cystamine dihyd...

(2,3,4,5,6-pentachlorophenyl) N-(2-chloroethyl)-N-nitrosocarbamate Structure

80354-53-6

(2,3,4,5,6-pent...

~75%

1-(2-chloroethyl)-3-[2-[2-[(2-chloroethyl-nitroso-carbamoyl)amino]ethy ldisulfanyl]ethyl]-1-nitroso-urea Structure

77469-44-4

1-(2-chloroethy...

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Cystamine dihydrochloride Structure

56-17-7

Cystamine dihyd...

CARBAMIC ACID, (2-CHLOROETHYL)NITROSO-, 2,5-DIOXO-1-PYRROLIDINYL ESTER Structure

80354-49-0

CARBAMIC ACID, ...

~75%

1-(2-chloroethyl)-3-[2-[2-[(2-chloroethyl-nitroso-carbamoyl)amino]ethy ldisulfanyl]ethyl]-1-nitroso-urea Structure

77469-44-4

1-(2-chloroethy...

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Cystamine dihydrochloride Structure

56-17-7

Cystamine dihyd...

pentafluorophenyl N-(2-chloroethyl)-N-nitrosocarbamate Structure

80354-55-8

pentafluorophen...

~76%

1-(2-chloroethyl)-3-[2-[2-[(2-chloroethyl-nitroso-carbamoyl)amino]ethy ldisulfanyl]ethyl]-1-nitroso-urea Structure

77469-44-4

1-(2-chloroethy...

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(2,5-dioxopyrrolidin-1-yl) N-(2-chloroethyl)carbamate Structure

80354-45-6

(2,5-dioxopyrro...

~93%

CARBAMIC ACID, (2-CHLOROETHYL)NITROSO-, 2,5-DIOXO-1-PYRROLIDINYL ESTER Structure

80354-49-0

CARBAMIC ACID, ...

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N/A Structure

2655-08-5

N/A

~94%

(2,3,4,5,6-pentachlorophenyl) N-methyl-N-nitrosocarbamate Structure

80354-52-5

(2,3,4,5,6-pent...

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Peratox Structure

87-86-5

Peratox

~%

(2,3,4,5,6-pentachlorophenyl) N-methyl-N-nitrosocarbamate Structure

80354-52-5

(2,3,4,5,6-pent...

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pentachlorophenyl N-(2-chloroethyl)carbamate Structure

80354-47-8

pentachlorophen...

~%

(2,3,4,5,6-pentachlorophenyl) N-(2-chloroethyl)-N-nitrosocarbamate Structure

80354-53-6

(2,3,4,5,6-pent...

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Peratox Structure

87-86-5

Peratox

~%

(2,3,4,5,6-pentachlorophenyl) N-(2-chloroethyl)-N-nitrosocarbamate Structure

80354-53-6

(2,3,4,5,6-pent...

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(2,4,5-trichlorophenyl) N-(2-chloroethyl)-N-nitroso-carbamate Structure

80354-51-4

(2,4,5-trichlor...

Cyclohexylamine Structure

108-91-8

Cyclohexylamine

~79%

Lomustine Structure

13010-47-4

Lomustine

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(2,3,4,5,6-pentachlorophenyl) N-(2-chloroethyl)-N-nitrosocarbamate Structure

80354-53-6

(2,3,4,5,6-pent...

Cyclohexylamine Structure

108-91-8

Cyclohexylamine

~82%

Lomustine Structure

13010-47-4

Lomustine

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Cyclohexylamine Structure

108-91-8

Cyclohexylamine

pentafluorophenyl N-(2-chloroethyl)-N-nitrosocarbamate Structure

80354-55-8

pentafluorophen...

~81%

Lomustine Structure

13010-47-4

Lomustine

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(3R,4R,5R,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol Structure

90-76-6

(3R,4R,5R,6R)-3...

(2,4,5-trichlorophenyl) N-(2-chloroethyl)-N-nitroso-carbamate Structure

80354-51-4

(2,4,5-trichlor...

~80%

2-((3-chloroethyl)-3-nitrosoureido)glucopyranose Structure

70866-07-8

2-((3-chloroeth...

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(3R,4R,5R,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol Structure

90-76-6

(3R,4R,5R,6R)-3...

(2,3,4,5,6-pentachlorophenyl) N-(2-chloroethyl)-N-nitrosocarbamate Structure

80354-53-6

(2,3,4,5,6-pent...

~81%

2-((3-chloroethyl)-3-nitrosoureido)glucopyranose Structure

70866-07-8

2-((3-chloroeth...

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(3R,4R,5R,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol Structure

90-76-6

(3R,4R,5R,6R)-3...

CARBAMIC ACID, (2-CHLOROETHYL)NITROSO-, 2,5-DIOXO-1-PYRROLIDINYL ESTER Structure

80354-49-0

CARBAMIC ACID, ...

~80%

2-((3-chloroethyl)-3-nitrosoureido)glucopyranose Structure

70866-07-8

2-((3-chloroeth...

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(3R,4R,5R,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol Structure

90-76-6

(3R,4R,5R,6R)-3...

pentafluorophenyl N-(2-chloroethyl)-N-nitrosocarbamate Structure

80354-55-8

pentafluorophen...

~81%

2-((3-chloroethyl)-3-nitrosoureido)glucopyranose Structure

70866-07-8

2-((3-chloroeth...

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