Magnesium nitride as a convenient source of ammonia: Preparation of pyrroles

Synlett

Volumn , Issue 17, 2008, Pages 2597-2600

  Veitch, Gemma E ^a   Bridgwood, Katy L ^a   Rands Trevor, Karen ^a   Ley, Steven V ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

Ammonia; Combinatorial chemistry; Heterocycles; Magnesium nitride; Pyrroles

Indexed keywords

1,4 DICARBONYL DERIVATIVE; 2 (4 BROMOPHENYL) 5 METHYL 1H PYRROLE; 2 (4 FLUOROPHENYL) 3 (4 METHOXYPHENYL) 5 (NAPHTHALEN 2 YL) 1H PYRROLE; 2 METHYL 5 [4 (TRIFLUOROMETHYL)PHENYL] 1H PYRROLE; 2 PHENYL 4,5 DIHYDRO 1H BENZO[G]INDOLE; 3 (THIOPHEN 2 YL) 2 4 TOLYL 5 [4 (TRIFLUOROMETHYL)PHENYL] 1H PYRROLE; AMMONIA; CARBONYL DERIVATIVE; MAGNESIUM NITRIDE; METHANOL; NITROGEN; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CYCLIZATION; POLYMERIZATION; SYNTHESIS;

EID: 55449097463     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0028-1083504     Document Type: Article

References (46)

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39. Representative Procedure for the Thermally Assisted Synthesis of 1H-Pyrroles (Table 2): To a stirred solution of 1-phenylpentane-1,4-dione (100 mg, 0.57 mmol) in MeOH (5.5 mL) at 0 °C was added magnesium nitride (143 mg, 1.43 mmol). The reaction vessel was sealed and heated to 80 °C for 24 h. After cooling to r.t., the reaction was subjected to workup and column chromatography as before.
40. 11BrN: 236.0077; found: 236.0080.
41. 3N: 226.0839; found: 226.0849.
42. General Procedure for the Thermally Assisted Synthesis of 1H-Pyrroles (Table 3): To a stirred solution of the 1,4-dicarbonyl compound (0.13 mmol) in MeOH (1.3 mL) at 0 °C was added magnesium nitride (1.3 mmol). The reaction vessel was sealed and allowed to stir for 10 min before heating to 80 °C for 24 h. After cooling to r.t., the reaction was subjected to workup and column chromatography as before. For pyrroles 10 and 11, neutral alumina was employed for chromatography to prevent decomposition.
43. 3S: 383.0956; found: 383.0960.
44. 15N: 245.1205; found: 245.1192.
45. 21NOF: 394.1607; found: 394.1617.
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