Synthesis of indoles by dehydrogenation of indolines

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

548492, C07D20904, C07D20930

Patent

active

055368433

ABSTRACT:
##STR1## By dehydrating indolines or their salts, the corresponding indoles having formula (I) are obtained. In the formula, R.sup.1 and R.sup.3 represent independently from each other hydrogen or alkyl groups with 1 to 4 C atoms, R.sup.2 stands for hydrogen, a methyl or a carboxyl group, R.sup.4 and R.sup.5 represent independently from each other hydrogen, amino groups, hydroxy groups, alkyl groups with 1 to 4 C atoms or alkoxy groups with 1 to 4 C atoms, or, in case R.sup.4 and R.sup.5 are bound to adjacent C atoms, both residues may also represent together an alkylene dioxy group with 1 to 4 C atoms. This process allows high yields of very pure indoles to be produced.

REFERENCES:
Russian Chemical Reviews vol. 36, No. 10, (1967), pp. 753-771 M. N. Preobrashenskaya `Synthesis of substituted indoles via indolines`.
Bull. Soc. Chim. Fr. (1966), pp. 1335-1342 M. Julia, H. Gaston-Brenton `Recherches en serie indolique. XVII.-Preparation de quelque indolines, indoles et tryptamines oxygenes en position -4 ou -6 par cyclisation "arynique"`.
J. Chem. Soc. (C) (1967) pp. 1424-1427 S. N. Mishra, G. A. Swan `Studies Related to the Chemistry of Melanins. Part III. Synthesis of 5,6-Dihydroxyindoline` see p. 1427.
Tetrahedron Lett. No. 10, (1970) pp. 723-726 T. Kametani et al. `A Novel Formation of the Indole Derivatives by Phenolic Oxidative Coupling`.
Biochem vol. 7. No. 5, (1968) pp. 1777-1786 M. Wilchek et al. `The Nonenzymatic Conversion of Tyrosine into Mono-and Dihydroxyindoles`.
J. Chem. Soc. (1950), pp. 1276-1282 J. Harley-Mason `The Chemistry of Adrenchrome and its Derivatives`.
B. P. Murphy, T. M. Schultz, J. Org. Chem. 50 (1985) 2790.
J. D. BuLock, J. Harley-Mason, J. Chem. Soc. (1951) 2248.
J. Harley-Mason, J. D. BuLock, Nature 166 (1950) 1036.
K. Wakamatsu, S. Ito, Anal. Biochem. 170 (1988) 335.
P. A. Wehrli, F. Pigott, U. Fischer, A. Kaiser, Helv. Chim. Acta 55 (1972) 3057.
J. Harley-Mason, J. Chem. Soc. (1953) 200.
R. J. S. Beer, K. Clarke, H. E. Khorana, A. Robertson, J. Chem. Soc. (1948) 2223.
H. Burton, J. A. Duffield, P. F. G. Praill, J. Chem. Soc. (1950) 1062.
J. D. Benigni, R. L. Minnis, J. Heterocycl. Chem. 2 (1965) 387.

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Synthesis of indoles by dehydrogenation of indolines does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Synthesis of indoles by dehydrogenation of indolines, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Synthesis of indoles by dehydrogenation of indolines will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-1785531

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.