Diels-Alder reactions of 1-azadienes

YS Cheng, AT Lupo Jr, FW Fowler

Index: Cheng,Y.S.; Lupo,A.T.; Fowler,F.W. Journal of the American Chemical Society, 1983 , vol. 105, p. 7696

Full Text: HTML

Citation Number: 77

Abstract

Abstract: N-Acyl-1-azadienes have been prepared by the thermal elimination of acetic acid from 0-acetylhydroxylamine derivatives. These reactive compounds have been observed to undergo the intramolecular Diels-Alder reaction to give piperidine derivatives. Studies on substituted azadienes suggest that the reaction follows predominantly an exo stereochemical pathway.

 Related Synthetic Route
2-(cyclopent-2-enyl)acetic acid chloride Structure

933-03-9

2-(cyclopent-2-...

(prop-2-enylamino) acetate Structure

87842-66-8

(prop-2-enylami...

~66%

[(2-cyclopent-2-en-1-ylacetyl)-prop-2-enylamino] acetate Structure

77413-82-2

[(2-cyclopent-2...

[acetyl(prop-2-enyl)amino] acetate Structure

87842-65-7

[acetyl(prop-2-...

~%

[(2-cyclopent-2-en-1-ylacetyl)-prop-2-enylamino] acetate Structure

77413-82-2

[(2-cyclopent-2...

[acetyl(prop-2-enyl)amino] acetate Structure

87842-65-7

[acetyl(prop-2-...

~67%

N-(1-methoxyprop-2-enyl)acetamide Structure

77413-86-6

N-(1-methoxypro...

acetamido acetate Structure

7340-09-2

acetamido acetate

1-(bromomethyl)cyclohex-1-ene Structure

37677-17-1

1-(bromomethyl)...

~66%

[acetyl(cyclohexen-1-ylmethyl)amino] acetate Structure

87842-89-5

[acetyl(cyclohe...

[pent-4-enoyl(prop-2-enyl)amino] acetate Structure

77413-79-7

[pent-4-enoyl(p...

~%

N-prop-2-enylpent-4-enamide Structure

87842-68-0

N-prop-2-enylpe...

4-Pentenoyl chloride Structure

39716-58-0

4-Pentenoyl chloride

~%

N-prop-2-enylpent-4-enamide Structure

87842-68-0

N-prop-2-enylpe...

N-(1-methoxyprop-2-enyl)acetamide Structure

77413-86-6

N-(1-methoxypro...

~%

Acetamide,N-2-propen-1-yl- Structure

692-33-1

Acetamide,N-2-p...

[acetyl(prop-2-enyl)amino] acetate Structure

87842-65-7

[acetyl(prop-2-...

~%

Acetamide,N-2-propen-1-yl- Structure

692-33-1

Acetamide,N-2-p...

4-Pentenoyl chloride Structure

39716-58-0

4-Pentenoyl chloride

(pent-3-en-2-ylamino) acetate Structure

87842-88-4

(pent-3-en-2-yl...

~31%

[pent-4-enoyl(pent-3-en-2-yl)amino] acetate Structure

87842-72-6

[pent-4-enoyl(p...

(E)-4-bromopent-2-ene Structure

56535-63-8

(E)-4-bromopent...

~%

[pent-4-enoyl(pent-3-en-2-yl)amino] acetate Structure

87842-72-6

[pent-4-enoyl(p...

[acetyl(pent-3-en-2-yl)amino] acetate Structure

87842-87-3

[acetyl(pent-3-...

~%

[pent-4-enoyl(pent-3-en-2-yl)amino] acetate Structure

87842-72-6

[pent-4-enoyl(p...

4-Pentenoyl chloride Structure

39716-58-0

4-Pentenoyl chloride

(cyclohexen-1-ylmethylamino) acetate Structure

87842-90-8

(cyclohexen-1-y...

~74%

[cyclohexen-1-ylmethyl(pent-4-enoyl)amino] acetate Structure

87842-77-1

[cyclohexen-1-y...

1-(bromomethyl)cyclohex-1-ene Structure

37677-17-1

1-(bromomethyl)...

~%

[cyclohexen-1-ylmethyl(pent-4-enoyl)amino] acetate Structure

87842-77-1

[cyclohexen-1-y...

[acetyl(cyclohexen-1-ylmethyl)amino] acetate Structure

87842-89-5

[acetyl(cyclohe...

~%

[cyclohexen-1-ylmethyl(pent-4-enoyl)amino] acetate Structure

87842-77-1

[cyclohexen-1-y...

4-Pentenoyl chloride Structure

39716-58-0

4-Pentenoyl chloride

(but-2-enylamino) acetate Structure

87842-86-2

(but-2-enylamin...

~86%

[but-2-enyl(pent-4-enoyl)amino] acetate Structure

87842-84-0

[but-2-enyl(pen...

[acetyl(but-2-enyl)amino] acetate Structure

87842-85-1

[acetyl(but-2-e...

~%

[but-2-enyl(pent-4-enoyl)amino] acetate Structure

87842-84-0

[but-2-enyl(pen...

[hex-5-enoyl(prop-2-enyl)amino] acetate Structure

77413-80-0

[hex-5-enoyl(pr...

~69%

1,2,3,8,9,9a-hexahydroquinolizin-4-one Structure

87842-80-6

1,2,3,8,9,9a-he...

hex-5-enoyl chloride Structure

36394-07-7

hex-5-enoyl chloride

~%

1,2,3,8,9,9a-hexahydroquinolizin-4-one Structure

87842-80-6

1,2,3,8,9,9a-he...

[pent-4-enoyl(prop-2-enyl)amino] acetate Structure

77413-79-7

[pent-4-enoyl(p...

~77%

2,7,8,8a-tetrahydro-1H-indolizin-3-one Structure

98065-13-5

2,7,8,8a-tetrah...

methyl [pent-4-enoyl(prop-2-enyl)amino] carbonate Structure

87842-69-1

methyl [pent-4-...

~65%

2,7,8,8a-tetrahydro-1H-indolizin-3-one Structure

98065-13-5

2,7,8,8a-tetrah...

4-Pentenoyl chloride Structure

39716-58-0

4-Pentenoyl chloride

~%

2,7,8,8a-tetrahydro-1H-indolizin-3-one Structure

98065-13-5

2,7,8,8a-tetrah...

N-hydroxy-N-prop-2-enylpent-4-enamide Structure

87842-83-9

N-hydroxy-N-pro...

~%

2,7,8,8a-tetrahydro-1H-indolizin-3-one Structure

98065-13-5

2,7,8,8a-tetrah...

N-prop-2-enylhydroxylamine Structure

52716-05-9

N-prop-2-enylhy...

4-Pentenoyl chloride Structure

39716-58-0

4-Pentenoyl chloride

~53%

N-hydroxy-N-prop-2-enylpent-4-enamide Structure

87842-83-9

N-hydroxy-N-pro...

crotyl bromide Structure

4784-77-4

crotyl bromide

acetamido acetate Structure

7340-09-2

acetamido acetate

~57%

[acetyl(but-2-enyl)amino] acetate Structure

87842-85-1

[acetyl(but-2-e...

[acetyl(but-2-enyl)amino] acetate Structure

87842-85-1

[acetyl(but-2-e...

~46%

(but-2-enylamino) acetate Structure

87842-86-2

(but-2-enylamin...

4-Pentenoyl chloride Structure

39716-58-0

4-Pentenoyl chloride

(prop-2-enylamino) acetate Structure

87842-66-8

(prop-2-enylami...

~88%

[pent-4-enoyl(prop-2-enyl)amino] acetate Structure

77413-79-7

[pent-4-enoyl(p...

[acetyl(prop-2-enyl)amino] acetate Structure

87842-65-7

[acetyl(prop-2-...

~%

[pent-4-enoyl(prop-2-enyl)amino] acetate Structure

77413-79-7

[pent-4-enoyl(p...

(prop-2-enylamino) acetate Structure

87842-66-8

(prop-2-enylami...

Allyl carbonochloridate Structure

2937-50-0

Allyl carbonoch...

~49%

[prop-2-enoxycarbonyl(prop-2-enyl)amino] acetate Structure

87842-63-5

[prop-2-enoxyca...

[acetyl(prop-2-enyl)amino] acetate Structure

87842-65-7

[acetyl(prop-2-...

~%

[prop-2-enoxycarbonyl(prop-2-enyl)amino] acetate Structure

87842-63-5

[prop-2-enoxyca...

(E)-4-bromopent-2-ene Structure

56535-63-8

(E)-4-bromopent...

~%

(pent-3-en-2-ylamino) acetate Structure

87842-88-4

(pent-3-en-2-yl...

[acetyl(pent-3-en-2-yl)amino] acetate Structure

87842-87-3

[acetyl(pent-3-...

~26%

(pent-3-en-2-ylamino) acetate Structure

87842-88-4

(pent-3-en-2-yl...

pent-4-ynoyl chloride Structure

55183-44-3

pent-4-ynoyl ch...

(prop-2-enylamino) acetate Structure

87842-66-8

(prop-2-enylami...

~51%

[pent-4-ynoyl(prop-2-enyl)amino] acetate Structure

87842-64-6

[pent-4-ynoyl(p...

[acetyl(prop-2-enyl)amino] acetate Structure

87842-65-7

[acetyl(prop-2-...

~%

[pent-4-ynoyl(prop-2-enyl)amino] acetate Structure

87842-64-6

[pent-4-ynoyl(p...

[acetyl(prop-2-enyl)amino] acetate Structure

87842-65-7

[acetyl(prop-2-...

~54%

(prop-2-enylamino) acetate Structure

87842-66-8

(prop-2-enylami...

[acetyl(cyclohexen-1-ylmethyl)amino] acetate Structure

87842-89-5

[acetyl(cyclohe...

~38%

(cyclohexen-1-ylmethylamino) acetate Structure

87842-90-8

(cyclohexen-1-y...

1-(bromomethyl)cyclohex-1-ene Structure

37677-17-1

1-(bromomethyl)...

~%

(cyclohexen-1-ylmethylamino) acetate Structure

87842-90-8

(cyclohexen-1-y...

hex-5-enoyl chloride Structure

36394-07-7

hex-5-enoyl chloride

(prop-2-enylamino) acetate Structure

87842-66-8

(prop-2-enylami...

~86%

[hex-5-enoyl(prop-2-enyl)amino] acetate Structure

77413-80-0

[hex-5-enoyl(pr...

[acetyl(prop-2-enyl)amino] acetate Structure

87842-65-7

[acetyl(prop-2-...

~%

[hex-5-enoyl(prop-2-enyl)amino] acetate Structure

77413-80-0

[hex-5-enoyl(pr...

(E)-4-bromopent-2-ene Structure

56535-63-8

(E)-4-bromopent...

acetamido acetate Structure

7340-09-2

acetamido acetate

~8%

[acetyl(pent-3-en-2-yl)amino] acetate Structure

87842-87-3

[acetyl(pent-3-...


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