Peter G. Houghton
Merck & Co.
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Tetrahedron | 1997
Peter E. Maligres; Ioannis N. Houpis; Kai Rossen; Audrey Molina; Jess W. Sager; Veena Upadhyay; Kenneth M. Wells; Robert A. Reamer; Joseph E. Lynch; David Askin; Ralph P. Volante; Paul J. Reider; Peter G. Houghton
Abstract The preparation of the Merck Growth Hormone Secretagogue; MK-677 is described. A Fischer indole/reduction based strategy provides the novel spiroindoline nucleus of this potent compound. This optimized sequence necessitates the isolation of only one intermediate 10 and provides MK-677 in 48% overall yield from isonipecotic acid 3.
Journal of The Chemical Society-perkin Transactions 1 | 1985
Peter G. Houghton; David F. Pipe; Charles W. Rees
1-(2-Nitrophenyl)-5-phenyltetrazole (5b) decomposes when heated to give nitrogen, carbon dioxide, and 2-phenylbenzotriazole (6) in high yield. This new molecular rearrangement proceeds via 2-nitrophenyl(phenyl)carbodi-imide (8). Other precursors of this carbodi-imide, i.e. oxadiazolone (10), oxadiazolethione (11), oxathiadiazole 2-oxide (12), and the aminimide (16), and carbodi-imide itself, all give 2-phenylbenzotriazole (6) on thermolysis, the last three in high yield. This reaction is general for diarylcarbodi-imides with an ortho nitro group, and their precursors, and it provides a useful new route to 2-arylbenzotriazoles. A sequence of electrocyclic ring closing and opening reactions (Scheme 5) is proposed as the mechanism of this process. The key intermediate, 2-phenyl-1,2,4-benzotriazin-3-one 1-oxide (19), has been isolated from a careful thermolysis of (12) in toluene; in solution it is in reversible equilibrium with the ring-opened form (20). This new nitro-carbodi-imide group interaction has been extended to the more stable nitrobiphenyl(phenyl)carbodi-imide (25) and nitronaphthyl(phenyl)-carbodi-imide (24) which, on flash vacuum pyrolysis, give benzimidazo[1,2-f]phenanthridine (29) and benz[cd]indazole 1-oxide (32) respectively, in new rearrangements.
Journal of The Chemical Society-perkin Transactions 1 | 1977
Alan O. Fitton; Jonathan Frost; Peter G. Houghton; Hans Suschitzky
The reactions of several 2- and 3-(aryliminomethyl)chromones with various chloroketens have been investigated. Whereas the 2-substituted chromones gave 2-(4-oxoazetidin-2-yl)chromones, the 3-substituted chromones yielded fused pyridone derivatives.
Journal of The Chemical Society-perkin Transactions 1 | 1993
Peter G. Houghton; Guy R. Humphrey; Derek J. Kennedy; D. Craig Roberts; Stanley H. B. Wright
An enantioselective synthesis of (4R)-1-azabicyclo[2.2.1]heptane derivatives is described commencing from readily available trans-4-hydroxy-L-proline which is converted into the key intermediate (3R)-N-(tert-butoxycarbonyl)-3-methylsulfonyloxypyrrolidine 4. Reaction of the sulfonate ester 4 with an enolate anion yields a mixture of (3R)-pyrrolidinylacetic esters 8 and 9 which are reduced to the corresponding alcohols 10 and 11. Conversion of the alcohols into the sulfonate esters 12 and 13 followed by deprotection of the pyrrolidine nitrogen leads to cyclisation yielding the (4R)-1- azabicyclo[2.2.1 ] heptane derivatives 14 and 15.
Journal of The Chemical Society-perkin Transactions 1 | 1989
Michael S. Ashwood; Jacqueline A. Gourlay; Peter G. Houghton; Madeleine A. Nagel; Stanley H. B. Wright
Novel 5,6-dihydro-4H-imidazo[1,5-a][4,1]benzoxazepin-6-ones have been prepared from benzoxazepindiones by 1,3-dipolar cycloadditions. Ring opening of the oxygen analogues with amines, chlorination followed by base promoted recyclisation provided 5,6-dihydro-4H-imidazo[1,5-a][1,4] benzodiazepin-6-ones by a novel route.
Journal of The Chemical Society-perkin Transactions 1 | 1979
Alan O. Fitton; Jonathan Frost; Peter G. Houghton; Hans Suschitzky
Whereas chromones are usually cleaved by amines. 3-(aryliminomethyl)chromones undergo nucleophilic addition with aromatic primary amines to give 2-amino-3-(arylaminomethylene)chroman-4-one derivatives. The 3-(aryliminomethyl) group also facilitates addition to the system of a variety of alcohols and thiols, and certain thiol adducts can be cyclised to thiazepine derivatives. The action of manganese dioxide on 3-(aryliminomethyl)chromones leads to 3-(arylaminomethylene)chroman-2,4-diones.
Journal of Heterocyclic Chemistry | 1991
Ian F. Cottrell; David Hands; Peter G. Houghton; Guy R. Humphrey; Stanley H. B. Wright
Archive | 1996
Peter G. Houghton; Ioannis N. Houpis; Audrey Molina; Joseph E. Lynch; Ralph P. Volante
Journal of Organic Chemistry | 2005
J. Michael Williams; Karel M. J. Brands; Renato T. Skerlj; Ronald B. Jobson; George Marchesini; Karen M. Conrad; Brenda Pipik; Kimberly A. Savary; Fuh-Rong Tsay; Peter G. Houghton; D. Richard Sidler; Ulf-H. Dolling; Lisa DiMichele; Thomas J. Novak
Journal of Organic Chemistry | 2002
Karel M. J. Brands; Ronald B. Jobson; Karen M. Conrad; J. Michael Williams; Brenda Pipik; Mark Cameron; Antony J. Davies; Peter G. Houghton; Michael S. Ashwood; Ian F. Cottrell; Robert A. Reamer; Derek J. Kennedy; Ulf-H. Dolling; Paul J. Reider