Regioselectivity of deprotonation of indoline and tetrahydroquinoline dithiocarbamic and carbamic compounds: A correction

Synthesis

Volumn , Issue 2, 1997, Pages 171-172

  Ahlbrecht, Hubertus ^a   Kornetzky, Dieter ^a   Purder, Thomas ^a   Katritzky, Alan R ^b   Ghiviriga, Ion ^b   Levell, Julian ^b  

^a JUSTUS LIEBIG UNIVERSITY   (Germany)

^b UNIVERSITY OF FLORIDA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; QUINOLINE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ERROR; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031055394     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1157     Document Type: Article

References (12)

1. Ahlbrecht, H.; Schmitt, C. Synthesis 1994, 983.
2. Ahlbrecht, H.; Kornetzky, D. Synthesis 1988, 775.
3. Katritzky, A. R.; Akutagawa, K. Tetrahedron 1986, 42, 2571.
4. Katritzky, A. R.; Sengupta, S. J. Chem. Soc., Perkin Trans. 1 1989, 17.
5. Prof. Hajime Katayama, Niigata College of Pharmacy, Niigata City, Japan. H. A. thanks colleague Katayama warmly for this information and for friendly help.
6. Ahlbrecht, H.; Kornetzky, D.; unpublished work. Kornetzky, D., Ph. D. Dissertation, Universität Gießen, 1990.
7. Ahlbrecht, H.; Kornetzky, D.; unpublished work. Kornetzky, D., Ph. D. Dissertation, Universität Gießen, 1990.
8. Indoline as well as tetrahydroquinoline can be deprotonated as formamidine at the α-position (Meyers, A. I.; Hellring, S. Tetrahedron Lett. 1981, 22, 5119. Meyers, A. I.; Milot, G. J. Org. Chem. 1993, 58, 6538) or N-Boc derivative at the orthoposition (Beak, P.; Lee, W.-K. Tetrahedron Lett. 1989, 30, 1197. Iwao, M.; Kuraishi, T. Heterocycles 1992, 34, 1031). If the ortho-position is blocked the N-Boc derivative is also deprotonated at the α-position. In both cases the structures are as described (Meyers, A. I.; private communication to H. A.). We thank colleagues Meyers and Beak for their cooperation.
9. Indoline as well as tetrahydroquinoline can be deprotonated as formamidine at the α-position (Meyers, A. I.; Hellring, S. Tetrahedron Lett. 1981, 22, 5119. Meyers, A. I.; Milot, G. J. Org. Chem. 1993, 58, 6538) or N-Boc derivative at the orthoposition (Beak, P.; Lee, W.-K. Tetrahedron Lett. 1989, 30, 1197. Iwao, M.; Kuraishi, T. Heterocycles 1992, 34, 1031). If the ortho-position is blocked the N-Boc derivative is also deprotonated at the α-position. In both cases the structures are as described (Meyers, A. I.; private communication to H. A.). We thank colleagues Meyers and Beak for their cooperation.
10. Indoline as well as tetrahydroquinoline can be deprotonated as formamidine at the α-position (Meyers, A. I.; Hellring, S. Tetrahedron Lett. 1981, 22, 5119. Meyers, A. I.; Milot, G. J. Org. Chem. 1993, 58, 6538) or N-Boc derivative at the orthoposition (Beak, P.; Lee, W.-K. Tetrahedron Lett. 1989, 30, 1197. Iwao, M.; Kuraishi, T. Heterocycles 1992, 34, 1031). If the ortho-position is blocked the N-Boc derivative is also deprotonated at the α-position. In both cases the structures are as described (Meyers, A. I.; private communication to H. A.). We thank colleagues Meyers and Beak for their cooperation.
11. Indoline as well as tetrahydroquinoline can be deprotonated as formamidine at the α-position (Meyers, A. I.; Hellring, S. Tetrahedron Lett. 1981, 22, 5119. Meyers, A. I.; Milot, G. J. Org. Chem. 1993, 58, 6538) or N-Boc derivative at the orthoposition (Beak, P.; Lee, W.-K. Tetrahedron Lett. 1989, 30, 1197. Iwao, M.; Kuraishi, T. Heterocycles 1992, 34, 1031). If the ortho-position is blocked the N-Boc derivative is also deprotonated at the α-position. In both cases the structures are as described (Meyers, A. I.; private communication to H. A.). We thank colleagues Meyers and Beak for their cooperation.
12. Indoline as well as tetrahydroquinoline can be deprotonated as formamidine at the α-position (Meyers, A. I.; Hellring, S. Tetrahedron Lett. 1981, 22, 5119. Meyers, A. I.; Milot, G. J. Org. Chem. 1993, 58, 6538) or N-Boc derivative at the orthoposition (Beak, P.; Lee, W.-K. Tetrahedron Lett. 1989, 30, 1197. Iwao, M.; Kuraishi, T. Heterocycles 1992, 34, 1031). If the ortho-position is blocked the N-Boc derivative is also deprotonated at the α-position. In both cases the structures are as described (Meyers, A. I.; private communication to H. A.). We thank colleagues Meyers and Beak for their cooperation.