Synthetic Communications

Tu, Shu-jiang; Zhou, Jian-Feng; Cai, Pei-jun; Wang, Hai; Feng, Jun-cai

doi: 10.1081/SCC-100108221pmid: N/A

A series of hexahydrocoumarins 4 were synthesized by the reaction of aromatic aldehyde, 5,5-dimethyl-1,3-cyclohexandione and meldiums acid under microwave irradiation without catalyst. The structure of 4a was determined by x-ray analysis.

Peng, Yanqing; Song, Gonghua; Qian, Xuhong

doi: 10.1081/SCC-100108222pmid: N/A

Efficient conversion of carbonyl compounds and pentaerythritol to corresponding diacetals in the presence of 12-tungstophosphoric acid under microwave irradiation is described.

Jaime-Figueroa, Saul; Zamilpa, Alejandro; Guzmán, Angel; Morgans, David J.

doi: 10.1081/SCC-100108223pmid: N/A

An easy and efficient synthesis of 3-alkyluracils is described. Thus, BOC-protection at N-1 of uracil permits selective alkylation at N-3. This protecting group can be removed under very mild conditions.

Singh, Shiv P.; Naithani, Rajesh; Aggarwal, Ranjana; Prakash, Om

doi: 10.1081/SCC-100108224pmid: N/A

Alpha-tosyloxyacetylthiophene (3), obtained by the hypervalent iodine oxidation of 2-acetylthiophene (2) using [hydroxy- (tosyloxy)iodo]benzene (HTIB), on treatment with rubeanic acid exclusively generates 4-(2-thienyl)thiazole-2-thiocarboxamide (4) which upon subsequent treatment with a variety of alpha-tosyloxyketones (5) affords the title compounds (6) in excellent yields.

Snider, Barry B.; O'Hare, Sean M

doi: 10.1081/SCC-100108225pmid: N/A

Reaction of β-keto ester 12 with 2 equiv. of Mn(OAc)32H2O in KOAc-buffered MeOH followed by acidic workup afforded 51% of tricyclic furan 14 indicating that oxidative cyclizations can be terminated by addition to furans. Reduction of 14 with LAH provided 7, completing a five-step formal synthesis of 15-acetoxypallescensin-A.

Cachoux, Frédéric; Ibrahim-Ouali, Malika; Santelli, Maurice

doi: 10.1081/SCC-100108226pmid: N/A

We described here an efficient and short new method to synthesize cyclopentanol derivatives. Ring opening of spiroepoxide 3 was done easily by an amine or ethyl carbamate leading to new molecules bifunctionalized. The characteristic 1H and 13C NMR spectroscopic features of the synthesized compounds are reported.

Shirini, F.; Azadbar, M. R.

doi: 10.1081/SCC-100108227pmid: N/A

Oximes, hydrazones and semicarbazones of benzylic aldehydes and ketones undergo facile cleavage to the corresponding carbonyl compounds by tris[tri-nitratocerium(IV)]paraperio- date, [(NO3)3Ce]3.H2IO6, in good to high yields.

Lee, Phil Ho; Bang, Keukchan; Lee, Kooyeon; Sung, Sun-young; Chang, Sukbok

doi: 10.1081/SCC-100108228pmid: N/A

Ultrasound promoted Reformatsky reaction by the reaction of aldehydes or ketone with ethyl bromoacetate in the presence of indium metal afforded β-hydroxyesters in good to excellent yields under mild conditions.

Cho, Chan Sik; Kim, Joon Seok; Kim, Hun Seol; Kim, Tae-Jeong; Shim, Sang Chul

doi: 10.1081/SCC-100108229pmid: N/A

Anilines react with an array of tetraalkylammonium halides in the presence of a catalytic amount of a ruthenium catalyst together with SnCl2·2H2O in dioxane at 180°C to afford selectively N-monoalkylanilines in good yields.

Broggini, Gianluigi; Molteni, Giorgio; Pilati, Tullio; Zecchi, Gaetano

doi: 10.1081/SCC-100108230pmid: N/A

Intramolecular cycloaddition of homochiral nitrilimines 8 was exploited to obtain enantiopure pyrrolo[3,4-c]pyrazole derivatives 9 and 10 with high overall yields.