Lonza Inc.

Ihara Chemical Industry Co., Ltd.

Gareth J Griffiths

Jacques Gosteli

Felix Previdoli

Rene Imwinkelried

Gerhard C Stucky

Hidetaka Hiyoshi

Aleksander Warm

Hans P Mettler

Lester Mills

Gary Ryan

Ren E Imwinkelried

Francis Djojo

Yves Guggisberg

A process for the preparation, of (pyrimidin-2-yl)methyl ketones of the general formula (I), in which Ris in each case a C-alkyl group, a C-cycloalkyl group, an allyl group or an aryl-C-alkyl group, and Ris a C-alkyl group or aryl group. For this, a malondiimidate of the general formula (II), in which Rhas the meaning given above, is reacted with a &#x3b2;-keto ester of the general formula (III), in which Rhas the meaning given above, and Ris a C-alkyl group. The compounds which can be prepared according to the invention are intermediates for the synthesis of agrochemical active ingredients.

Process for the preparation of (pyrimidin-2-yl) methyl ketones

A process for the preparation of 1-(pyrimidin-2-yl)propan-2-ones of general formula (I), in which R is in each case a C-alkyl group, a C-cycloalkyl group, an alkyl group or an aryl-C-alkyl group. For this, a malondiimidate of the general formula (II), in which R has the meaning given above, is reacted with diketene. The compounds which can be prepared according to the invention are intermediates for the synthesis of agrochemical active ingredients. 

Process for the preparation of 1-(pyrimidin-2-yl)propan-2-ones

A process for the preparation of 2-substituted 5-chloroimidazole-4-carbaldehydes of the general formula: ##STR1## wherein R is hydrogen, an alkyl group, an alkenyl group, a cycloalkyl group, a benzyl group or a phenyl group. The imidazole compounds are important starting products for the preparation of hypotensive pharmaceuticals or herbicides.

Process for the preparation of optionally 2-substituted

A process for the preparation of 2-substituted 5-chloroimidazole-4-carbaldehydes of the general formula: ##STR1## in which glycine is reacted with an imido ester of the general formula: ##STR2## and the resultant intermediate is converted into the product by a Vilsmeier reagent. The 2-substituted 5-chloroimidazole-4-carbaldehydes are valuable intermediates for the preparation of pharmaceuticals or herbicidally active compounds.

Process for the production of 2-substituted

A process for the preparation of 2-substituted 5-chloroimidazole-4-carbaldehydes of the general formula: ##STR1## wherein R is hydrogen, an alkyl group, an alkenyl group, a cycloalkyl group, a benzl group or a phenyl group. The imidazole compounds are important starting products for the preparation of hypotensive pharmaceuticals or herbicides.

2-Substituted 5-chlorimidazoles of the general formula: ##STR1## are new intermediate products for the production of antihyperintensive pharmaceutical agents or of herbicidal compounds. A process for the production of these intermediate products as well as a new process for the further reaction of 2-substituted 5-chlorimidazoles of general formula I, wherein R.sub.1 is hydrogen, to the 2-substituted 5-chlorimidazole-4-carbaldehydes of the formula: ##STR2##

A process for preparing 2-substituted 5-chloroimidazole-4-carbaldehydes of the general formula: ##STR1## In the process, a glycine ester hydrohalide is ring-closed with an imidate ester to obtain the intermediate 2-substituted 3,5-dihydroimidazol-4-one. This intermediate is converted with an N,N-substituted formamide acetel into an N,N-substituted aminomethyleneimidazolinone. This latter intermediate is chlorinated with phosphorus oxychloride or phosgene to obtain the final product 2-substituted 5-chlorimidazole-4-carbaldehydes of the general formula I. Also disclosed are N,N-substituted aminomethyleneimidazolinones of the general formula: ##STR2## wherein R is hydrogen or is an alkyl group, an alkenyl group, a cycloalkyl group, an arylalkyl group or an aryl group, and R.sub.5 and R.sub.6 are identical or different and each is an alkyl group or an aryl group, in the form of the E- or Z-isomer.

Process for the preparation of 2-substituted

The 2-substituted 5-chlorimidazoles of general formula: ##STR1## are new intermediate products for the production of antihypertensive pharmaceutical agents or of herbicidal compounds. A process for the production of these intermediate products as well as a new process for the further reaction of 2-substituted 5-chlorimidazoles of general formula I, wherein R.sub.1 is hydrogen, to the 2-substituted 5-chlorimidazole-4-carbaldehydes of general formula: ##STR2##

Process for producing 2-substituted 5-chlorimidazoles

A process for preparing 2-substituted 5-chloroimidazole-4-carbaldehydes of the general formula: ##STR1## In the process, a glycine ester hydrohalide is ring-closed with an imidate ester to obtain the intermediate 2-substituted 3,5-dihydroimidazol-4-one. This intermediate is converted with an N,N-substituted formamide acetal into an N,N-substituted aminomethyleneimidazolinone. This latter intermediate is chlorinated with phosphorus oxychloride or phosgene to obtain the final product 2-substituted 5-chlorimidazole-4-carbaldehydes of the general formula I. Also disclosed are N,N-substituted aminomethyleneimidazolinones of the general formula: ##STR2## wherein R is hydrogen or is an alkyl group, an alkenyl group, a cycloalkyl group, an arylalkyl group or an aryl group, and R.sub.5 and R.sub.6 are identical or different and each is an alkyl group or an aryl group, in the form of the E- or Z-isomer.

2-substituted 5-chlorimidazoles

Process for the production of 2-substituted 5-chlorimidazole-4-carbaldehydes of general formula: ##STR1## wherein R is alkyl, cycloalkyl, benzyl, or phenyl. These compounds form valuable intermediate products for the production of antihypertensive pharmaceutical agents or herbicidal compounds.

Process for the production of

A process for the production of 2-substituted 5-chlorimidazole-4-carbaldehydes of the general formula: ##STR1## wherein R is hydrogen, an alkyl group, and alkenyl group, a cycloalkyl group, a benzyl group, a phenyl group or an aryl group. These compounds form important intermediate products for the production of antihypertensive pharmaceutical agents or herbicidal compounds.

.beta.,.gamma.-unsaturated .delta.-lactams, especially 2-azabicyclo[2.2.1]hept-5-en-3-one, are produced by Diels-Alder reaction of 1,3-dienes with sulfonyl cyanides and subsequent hydrolysis. The sulfonyl cyanides were formed in situ from cyanogen chloride and the corresponding sulfinates. By the renewed reaction of the sulfinate formed in the hydrolysis of the Diels-Alder adducts with cyanogen chloride, the sulfonyl cyanides are regenerated and a catalytic cyclic process results. The 2-azabicyclo[2.2.1]hept-5-en-3-one is a starting compound in the synthesis of antiviral nucleoside analogs.

Process for the production of lactams

2-Azabicyclo[2.2.1]hept-5-en-3-one is produced by Diels-Alder reaction of cyclopentadiene and methanesulfonyl cyanide and then hydrolytic cleavage of the methanesulfonyl group.

Process for the production of 2-azabicyclo [2.2.1] hept-5-en-3-one

A process for the production of 1-(N-methanesulfonyl-N-methylaminosulfonyl)-3-(2-pyrimidyl) urea derivatives (MMSPH). In the process, methanesulfonylmethylamine (MMSA) is first converted with chlorosulfonylisocyanata (CSI) into a 1-methanesulfonyl-1-methyl-3- (N-methanesulfonyl-N-methylaminosulfonyl) urea derivative (MMMSH) and then the MMMSH is converted with a 2-aminopyridine into the end product.

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Gareth J Griffiths