2-amino-3-aroyl-benzo[.beta.]thiophenes and methods for preparin

Details 2-amino-3-aroyl-benzo[.beta.]thiophenes and methods for preparin 2-amino-3-aroyl-benzo[.beta.]thiophenes and methods for preparin

1994-06-10

1995-05-30

O'Sullivan, Peter

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

558230, C07C32744

Patent

active

054203490

ABSTRACT:
A group of 2-amino-3-aroyl-benzo[.beta.]thiophenes are prepared by preparing an .alpha.-hydroxy thioacetamide by silyl mediated condensation of an aldehyde with an anion of dialkylamino thioformamide, cyclizing the .alpha.-hydroxy thioamide, and subsequently acylating the benzo[.beta.]thiophene to yield the 2-amino-3-aryl derivative. These compounds may be treated with suitable phenyl Grignard reagents, and after deprotection, yield 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[.beta .]thiophene.

REFERENCES:
patent: 4133814 (1979-01-01), Jones et al.
patent: 4380635 (1983-04-01), Peters
patent: 4418068 (1983-11-01), Jones
Geffken et al. Chem Abstracts 109:37500 (1988).
Ablenas et al., "Destabilized Carbocations", Can. J. Chem., 65, 1800-1803 (1987).
Chippendale et al., "Condensed Thiophen Ring Systems", J. C. S. Perkin I, 1168-1172 (1974).
Reynaud et al., Bul. Soc. Chem. Fr., 3623-3628 (1965).
Creary et al. "The Nature of Cationic Intermediates Derived From .alpha.-Thiocarbonyl Meglates", J. Org. Chem. 51, 7-15 (1986).
Schauman "Synthesis of Thioamides and Thiolactams", Comp. Org. Syn, vol. 6 419-434 (1990).
Cholod, "Cyanohydrins", Kirk-othmer Encyclopedia of Chem Tech., vol. 7 3rd Ed. John Wiley & Sons, N.Y. 385-397 (1979).
Kobayashi et al., "A Facile Synthesis of Cyanohydrin Trimethylsilyl Ethers by the Addition Reaction of Trimethylsilyl cyanides with aldehydes under Basic Condition," Chem. Lett., 537-540 (1991).
Tinapp, Chem. Ber., 104, 2266-2272 (1971).

Affiliated with

Also associated with

Rating

2-amino-3-aroyl-benzo[.beta.]thiophenes and methods for preparin does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with 2-amino-3-aroyl-benzo[.beta.]thiophenes and methods for preparin, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and 2-amino-3-aroyl-benzo[.beta.]thiophenes and methods for preparin will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-363713