Palladium-catalyzed intramolecular addition of amines to acetylenes. Synthesis of cyclic imines

Y Fukuda, S Matsubara, K Utimoto

Index: Fukuda, Yukitoshi; Matsubara, Seijiro; Utimoto, Kiitiro Journal of Organic Chemistry, 1991 , vol. 56, # 20 p. 5812 - 5816

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Citation Number: 70

Abstract

Intramolecular aminopalladation of alkynylamines gave intermediary alkenylpalladium compounds that hydrolyzed and isomerized to thermodynamically stable cyclic imines. Treatment of 3-alkynylamines with a catalytic amount of PdC1z (MeCN) z gave exclusively 1- pyrrolines in good yields; 5-alkynylamines afforded 2, 3, 4, 5-tetrahydropyidines selectively. Treatment of 4-alkynylamines with Pd (I1) afforded mixtures of both 5-and 6-membered ...

 Related Synthetic Route
5-octynylamine Structure

135469-74-8

5-octynylamine

~65%

gamma-coniceine Structure

1604-01-9

gamma-coniceine

ω-azido-1-phenyl-1-hexyne Structure

856120-87-1

ω-azido-1-pheny...

~%

6-phenylhex-5-yn-1-amine Structure

135469-76-0

6-phenylhex-5-y...

4-PHENYL-3-BUTYN-1-OL Structure

10229-11-5

4-PHENYL-3-BUTY...

~%

2H-Pyrrole,3,4-dihydro-5-phenyl- Structure

700-91-4

2H-Pyrrole,3,4-...

4-methylbenzenesulfonic acid,4-phenylbut-3-yn-1-ol Structure

85375-43-5

4-methylbenzene...

~%

2H-Pyrrole,3,4-dihydro-5-phenyl- Structure

700-91-4

2H-Pyrrole,3,4-...

N/A Structure

199276-69-2

N/A

~%

2H-Pyrrole,3,4-dihydro-5-phenyl- Structure

700-91-4

2H-Pyrrole,3,4-...

dodec-4-yn-2-ol Structure

135469-87-3

dodec-4-yn-2-ol

~%

dodec-4-yn-2-amine Structure

138769-82-1

dodec-4-yn-2-amine

N/A Structure

98551-99-6

N/A

~72%

5-butyl-3,4-dihydro-2H-pyrrole Structure

64319-86-4

5-butyl-3,4-dih...

3-Octyn-1-ol Structure

14916-80-4

3-Octyn-1-ol

~%

5-butyl-3,4-dihydro-2H-pyrrole Structure

64319-86-4

5-butyl-3,4-dih...

1-azidooct-3-yne Structure

314773-72-3

1-azidooct-3-yne

~%

5-butyl-3,4-dihydro-2H-pyrrole Structure

64319-86-4

5-butyl-3,4-dih...

4-methylbenzenesulfonic acid,oct-3-yn-1-ol Structure

100419-71-4

4-methylbenzene...

~%

5-butyl-3,4-dihydro-2H-pyrrole Structure

64319-86-4

5-butyl-3,4-dih...

N/A Structure

138769-80-9

N/A

~%

dodec-4-yn-2-amine Structure

138769-82-1

dodec-4-yn-2-amine

1-ethyl-3-nonynylamine Structure

135469-77-1

1-ethyl-3-nonyn...

~72%

2-ethyl-5-pentyl-3,4-dihydro-2H-pyrrole Structure

61772-95-0

2-ethyl-5-penty...

Hept-1-yne Structure

628-71-7

Hept-1-yne

~%

2-ethyl-5-pentyl-3,4-dihydro-2H-pyrrole Structure

61772-95-0

2-ethyl-5-penty...

undec-5-yn-3-ol Structure

135469-85-1

undec-5-yn-3-ol

~%

2-ethyl-5-pentyl-3,4-dihydro-2H-pyrrole Structure

61772-95-0

2-ethyl-5-penty...


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