Tetrahedron

Carbon transfer reactions with heterocycles-V. A facile synthesis of nifedipine and analogues

H Singh, K Singh

Index: Singh, Harjit; Singh, Kamaljit Tetrahedron, 1989 , vol. 45, # 12 p. 3967 - 3974

Full Text: HTML

Citation Number: 21

Abstract

Download full text in PDF Opens in a new window. Article suggestions will be shown in a dialog on return to ScienceDirect. ... Please enable JavaScript to use all the features on this page. ... Oxazolidines and tetrahydro-(2H)-1,3-oxazines transfer their C(2) units at the carbonyl group oxidation level to alkyl-β-amino/anilinocrotonates to form1,4-dihydropyridines elaborated at C-4. ... Substituents in these reagents do not affect the mode of reaction.

 Related Synthetic Route
2H-1,3-Oxazine,tetrahydro- Structure

14558-49-7

2H-1,3-Oxazine,...

Ethyl (2Z)-3-amino-2-butenoate Structure

626-34-6

Ethyl (2Z)-3-am...

~88%

Diludine Structure

1149-23-1

Diludine

3-Phenyloxazolidine Structure

20503-92-8

3-Phenyloxazolidine

Ethyl (2Z)-3-amino-2-butenoate Structure

626-34-6

Ethyl (2Z)-3-am...

~80%

Diludine Structure

1149-23-1

Diludine

Ethyl (2Z)-3-amino-2-butenoate Structure

626-34-6

Ethyl (2Z)-3-am...

2-benzyl-4,4,6-trimethyltetrahydro-(2H)-1,3-oxazine Structure

36873-30-0

2-benzyl-4,4,6-...

~73%

3,5-Pyridinedicarboxylicacid, 1,4-dihydro-2,6-dimethyl-4-(phenylmethyl)-, 3,5-diethyl ester Structure

1539-57-7

3,5-Pyridinedic...

Ethyl 3-anilinocrotonate Structure

6287-35-0

Ethyl 3-anilino...

2H-1,3-Oxazine,tetrahydro-2-phenyl- Structure

17762-72-0

2H-1,3-Oxazine,...

~61%

diethyl 2,6-dimethyl-1,4-diphenyl-4H-pyridine-3,5-dicarboxylate Structure

53219-37-7

diethyl 2,6-dim...

2,4,4,6-tetramethyl-1,3-oxazinane Structure

74955-84-3

2,4,4,6-tetrame...

Ethyl (2Z)-3-amino-2-butenoate Structure

626-34-6

Ethyl (2Z)-3-am...

~59%

Diethyl 1,4-dihydro-2,4,6-trimethyl-3,5-pyridinedicarboxylate Structure

632-93-9

Diethyl 1,4-dih...

2-methyl-3-phenyl-1,3-oxazolidine Structure

16250-89-8

2-methyl-3-phen...

Ethyl (2Z)-3-amino-2-butenoate Structure

626-34-6

Ethyl (2Z)-3-am...

~55%

Diethyl 1,4-dihydro-2,4,6-trimethyl-3,5-pyridinedicarboxylate Structure

632-93-9

Diethyl 1,4-dih...

4,4-dimethyl-2-phenyl-1,3-oxazolidine Structure

20515-61-1

4,4-dimethyl-2-...

Ethyl (2Z)-3-amino-2-butenoate Structure

626-34-6

Ethyl (2Z)-3-am...

~69%

3,5-Pyridinedicarboxylicacid, 1,4-dihydro-2,6-dimethyl-4-phenyl-, 3,5-diethyl ester Structure

1165-06-6

3,5-Pyridinedic...

Ethyl (2Z)-3-amino-2-butenoate Structure

626-34-6

Ethyl (2Z)-3-am...

N/A Structure

13608-31-6

N/A

~70%

3,5-Pyridinedicarboxylicacid, 1,4-dihydro-2,6-dimethyl-4-phenyl-, 3,5-diethyl ester Structure

1165-06-6

3,5-Pyridinedic...

2H-1,3-Oxazine,tetrahydro-2-phenyl- Structure

17762-72-0

2H-1,3-Oxazine,...

Ethyl (2Z)-3-amino-2-butenoate Structure

626-34-6

Ethyl (2Z)-3-am...

~69%

3,5-Pyridinedicarboxylicacid, 1,4-dihydro-2,6-dimethyl-4-phenyl-, 3,5-diethyl ester Structure

1165-06-6

3,5-Pyridinedic...

2H-1,3-Oxazine,tetrahydro-4,4,6-trimethyl-2-phenyl- Structure

31771-33-2

2H-1,3-Oxazine,...

Ethyl (2Z)-3-amino-2-butenoate Structure

626-34-6

Ethyl (2Z)-3-am...

~71%

3,5-Pyridinedicarboxylicacid, 1,4-dihydro-2,6-dimethyl-4-phenyl-, 3,5-diethyl ester Structure

1165-06-6

3,5-Pyridinedic...

4-Nitrobenzaldehyde Structure

555-16-8

4-Nitrobenzaldehyde

~%

dimethyl 2,6-dimethyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Structure

21829-09-4

dimethyl 2,6-di...

Methyl (Z)-3-aminocrotonate Structure

21731-17-9

Methyl (Z)-3-am...

2-(o-nitro)phenyl-tetrahydro-(2H)-1,3-oxazine Structure

124732-84-9

2-(o-nitro)phen...

~74%

Nifedipine Structure

21829-25-4

Nifedipine

Methyl (Z)-3-aminocrotonate Structure

21731-17-9

Methyl (Z)-3-am...

2-(o-nitro)phenyl-4,4-dimethyloxazolidine Structure

124732-83-8

2-(o-nitro)phen...

~67%

Nifedipine Structure

21829-25-4

Nifedipine


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