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13.18.9.1.1.1.1 Method 1: By [3 + 2] Cyclocondensation with (Chloromethyl)dichlorophosphine

DOI: 10.1055/sos-SD-013-01026

Bansal, R. K.; Neelima Gupta, Science of Synthesis, (200413708.

4,5-Dihydro-1,3-thiazol-2-amine condenses regiospecifically with (chloromethyl)dichlorophosphine in the presence of triethylamine to give 5,6-dihydrothiazolo[2,3-e][1,4,2]diazaphosphole (55). However, thiazol-2-amine and benzothiazol-2-amine each form a mixture of two regioisomers under these conditions, the extent of regioselectivity in the latter case depending on the nature of any substituent group in the benzene ring (Scheme 22).[‌126‌,‌128‌] This method makes 3-unsubstituted products accessible.

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